Heterocyclic compound and organic light-emitting device including the same

ABSTRACT

Provided are a heterocyclic compound and an organic light-emitting device including the same. The heterocyclic compound includes a fluoro-containing cyclic group. The heterocyclic compound does not include a carbazole group, a dibenzofuran group, a dibenzothiophene group, and/or a triphenylene group. The organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an organic layer, the organic layer including an emission layer and at least one of the heterocyclic compound.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2017-0078597, filed on Jun. 21, 2017, in the KoreanIntellectual Property Office, the entire content of which isincorporated herein by reference.

BACKGROUND 1. Field

One or more embodiments relate to a heterocyclic compound and an organiclight-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices include self-emission devices that havewide viewing angles, high contrast ratios, short response times, andexcellent characteristics in terms of brightness, driving voltage, andresponse speed, as compared to other devices in the art.

An example of such an organic light-emitting device may include a firstelectrode disposed on a substrate, and a hole transport region, anemission layer, an electron transport region, and a second electrode,which are sequentially disposed on the first electrode. Holes providedfrom the first electrode may move toward the emission layer through thehole transport region, and electrons provided from the second electrodemay move toward the emission layer through the electron transportregion. Carriers, such as holes and electrons, recombine in the emissionlayer to produce excitons. These excitons transit (e.g., relax) from anexcited state to a ground state, thereby generating light.

SUMMARY

Aspects of embodiments of the present disclosure provide a novelheterocyclic compound and an organic light-emitting device including thesame.

Additional aspects of embodiments will be set forth in part in thedescription which follows and, in part, will be apparent from thedescription, or may be learned by practice of the presented embodiments.

An aspect of an embodiment of the present disclosure provides aheterocyclic compound represented by Formula 1 below:

In Formula 1,

L₁ to L₃ may each independently be a single bond, a substituted orunsubstituted C₃-C₆₀ carbocyclic group, or a substituted orunsubstituted C₁-C₆₀ heterocyclic group,

a1 to a3 may each independently be an integer from 1 to 5,

R₁ to R₃ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₂-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₂-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₂-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), and —B(Q₁)(Q₂),

b1 to b3 may each independently be an integer from 1 to 20,

at least one selected from R₁ to R₃ may be a fluoro-containing cyclicgroup,

when at least one of R₁(s) in the number of b1 is the fluoro-containingcyclic group, L₁ may not be a substituted or unsubstituted triazinegroup, when at least one of R₂(s) in the number of b2 is thefluoro-containing cyclic group, L₂ may not be a substituted orunsubstituted triazine group, and when at least one of R₃(s) in thenumber of b3 is the fluoro-containing cyclic group, L₃ may not be asubstituted or unsubstituted triazine group,

the heterocyclic compound may not include a carbazole group, adibenzofuran group, a dibenzothiophene group, and/or a triphenylenegroup,

at least one substituent of the substituted C₃-C₆₀ carbocyclic group,the substituted C₁-C₆₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₃-C₁₀ cycloalkyl group, the substituted C₂-C₁₀ heterocycloalkyl group,the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₂-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group,the substituted C₂-C₆₀ heteroaryl group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group may be selected from:

deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group,an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₆₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃),—N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), and —C(═O)(Q₁₁);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₆₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₆₀ heterocycloalkyl group, a C₃-C₆₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, each substituted with at least oneselected from deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, a biphenyl group, a terphenyl group,—Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), and —C(═O)(Q₂₁); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), and —C(═O)(Q₃₁),

Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independentlybe selected from hydrogen, deuterium, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryl groupsubstituted with a C₁-C₆₀ alkyl group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, a biphenyl group, and aterphenyl group, and

* indicates a binding site to a neighboring atom.

Another aspect of an embodiment of the present disclosure provides anorganic light-emitting device including: a first electrode; a secondelectrode facing the first electrode; and an organic layer between thefirst electrode and the second electrode and including an organic layer,wherein the organic layer includes an emission layer and at least one ofthe heterocyclic compound.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects of embodiments will become apparent and morereadily appreciated from the following description of the embodiments,taken in conjunction with the accompanying drawings in which:

FIG. 1 is a schematic view of an organic light-emitting device accordingto an embodiment;

FIG. 2 is a schematic view of an organic light-emitting device accordingto an embodiment;

FIG. 3 is a schematic view of an organic light-emitting device accordingto an embodiment; and

FIG. 4 is a schematic view of an organic light-emitting device accordingto an embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of whichare illustrated in the accompanying drawings, wherein like referencenumerals refer to like elements throughout. In this regard, the presentembodiments may have different forms and should not be construed asbeing limited to the descriptions set forth herein. Accordingly, theembodiments are merely described below, by referring to the drawings, toexplain aspects of embodiments of the present description. As usedherein, the term “and/or” includes any and all combinations of one ormore of the associated listed items. Expressions such as “at least oneof,” when preceding a list of elements, modify the entire list ofelements and do not modify the individual elements of the list.

A heterocyclic compound according to an embodiment is represented byFormula 1 below:

In Formula 1,

L₁ to L₃ may each independently be a single bond, a substituted orunsubstituted C₃-C₆₀ carbocyclic group, or a substituted orunsubstituted C₁-C₆₀ heterocyclic group.

In one embodiment, L₁ to L₃ may each independently be selected from:

a single bond, a benzene group, a pentalene group, an indene group, anaphthalene group, an azulene group, a heptalene group, an indacenegroup, an acenaphthalene group, a fluorene group, a spiro-bifluorenegroup, a spiro-benzofluorene-fluorene group, a benzofluorene group, adibenzofluorene group, a phenalene group, a phenanthrene group, ananthracene group, a fluoranthene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, a pyrrolegroup, a thiophene group, a furan group, a silole group, an imidazolegroup, a pyrazole group, a thiazole group, an isothiazole group, anoxazole group, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, a triazine group, a benzofurangroup, a benzothiophene group, a benzosilole group, a dibenzosilolegroup, a quinoline group, an isoquinoline group, a benzimidazole group,an imidazopyridine group, and an imidazopyrimidine group;

a benzene group, a pentalene group, an indene group, a naphthalenegroup, an azulene group, a heptalene group, an indacene group, anacenaphthalene group, a fluorene group, a spiro-bifluorene group, aspiro-benzofluorene-fluorene group, a benzofluorene group, adibenzofluorene group, a phenalene group, a phenanthrene group, ananthracene group, a fluoranthene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, a pyrrolegroup, a thiophene group, a furan group, a silole group, an imidazolegroup, a pyrazole group, a thiazole group, an isothiazole group, anoxazole group, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, a triazine group, a benzofurangroup, a benzothiophene group, a benzosilole group, a dibenzosilolegroup, a quinoline group, an isoquinoline group, a benzimidazole group,an imidazopyridine group, and an imidazopyrimidine group, eachsubstituted with at least one selected from deuterium, —Cl, —Br, —I, ahydroxyl group, a cyano group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, a heptalenyl group, an indacenylgroup, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coronenyl group, anovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzofuranyl group,a benzothiophenyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and—B(Q₃₁)(Q₃₂), and

Q₁ and Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, and a pyridinyl group.

For example, L₁ to L₃ may each independently be selected from a singlebond and groups represented by Formulae 3-1 to 3-29, but embodiments ofthe present disclosure are not limited thereto:

In Formulae 3-1 to 3-29,

Y₁ may be C(Z₃)(Z₄) or Si(Z₆)(Z₇),

Z₁ to Z₇ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₂₀ alkyl group,a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, a silolyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, adibenzosilolyl group, and —Si(Q₃)(Q₃₂)(Q₃₃),

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₂₀ alkyl group,a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, and a pyridinyl group,

d2 may be an integer from 0 to 2,

d3 may be an integer from 0 to 3,

d4 may be an integer from 0 to 4,

d6 may be an integer from 0 to 6,

d8 may be an integer from 0 to 8, and

* and *′ each indicate a binding site to a neighboring atom.

a1 to a3 in Formula 1 may each independently be an integer from 1 to 5,wherein, when a2 is two or more, two or more L₂(s) may be identical toor different from each other, when a2 is two or more, two or more L₂(s)may be identical to or different from each other, and when a3 is two ormore, two or more L₃(s) may be identical to or different from eachother.

In one embodiment, a1 to a3 may each independently be an integer from 1to 3.

R₁ to R₃ in Formula 1 may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid groupor a salt thereof, a phosphoric acid group or a salt thereof, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₂-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₂-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), and —B(Q₁)(Q₂).

In one embodiment, R₁ to R₃ may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a pyrenyl group, a chrysenyl group, anaphthacenyl group, a picenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a rubicenyl group, acoronenyl group, an ovalenyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, athiophenyl group, a furanyl group, a quinolinyl group, an isoquinolinylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzosilolylgroup, a benzonaphthosilolyl group, a dinaphthosilolyl group, abenzimidazolyl group, a phenanthrolinyl group, and an imidazopyridinylgroup;

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a pyrenyl group, a chrysenyl group, anaphthacenyl group, a picenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a rubicenyl group, acoronenyl group, an ovalenyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, athiophenyl group, a furanyl group, a quinolinyl group, an isoquinolinylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzosilolylgroup, a benzonaphthosilolyl group, a dinaphthosilolyl group, abenzimidazolyl group, a phenanthrolinyl group, and an imidazopyridinylgroup, each substituted with at least one selected from deuterium, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a biphenyl group, a terphenyl group, a pentalenyl group, anindenyl group, a naphthyl group, an azulenyl group, a heptalenyl group,an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a pyrenyl group, a chrysenyl group, anaphthacenyl group, a picenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a rubicenyl group, acoronenyl group, an ovalenyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, athiophenyl group, a furanyl group, a quinolinyl group, an isoquinolinytgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzosilolylgroup, —N(Q₃₁)(Q₃₂), and —Si(Q₃₁)(Q₃₂)(Q₃₃); and

—N(Q₁)(Q₂) and —B(Q₁)(Q₂), and

Q₁, Q₂, and Q₃₁ to Q₃₃ may each independently be selected from:

a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, and a pyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group,and a pyridinyl group, each substituted with a C₁-C₂₀ alkyl group or aC₁-C₂₀ alkoxy group.

b1 to b3 in Formula 1 may each independently be an integer from 1 to 20,wherein, when b1 is two or more, two or more R₁(s) may be identical toor different from each other, when b2 is two or more, two or more R₂(s)may be identical to or different from each other, and when b3 is two ormore, two or more R₃(s) may be identical to or different from eachother.

For example, b1 to b3 may each independently be an integer from 1 to 4.

at least one selected from R₁ to R₃ in Formula 1 may be afluoro-containing cyclic group (e.g., a cyclic group containing at leastone fluorine atom). The “fluoro-containing cyclic group” may include,for example, a C₃-C₆₀ carbocyclic group substituted with at least one —For a C₁-C₆₀ heterocyclic group substituted with at least one —F. The“C₃-C₆₀ carbocyclic group substituted with at least one —F” may include,for example, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, anda monovalent non-aromatic condensed polycyclic group, each substitutedwith at least one —F, and the “C₁-C₆₀ heterocyclic group substitutedwith at least one —F” may include, for example, a C₂-C₁₀heterocycloalkyl group, a C₂-C₁₀ heterocycloalkenyl group, a C₂-C₆₀heteroaryl group, and a monovalent non-aromatic condensedheteropolycyclic group, each substituted with at least one —F.

In Formula 1, when at least one of R₁(s) in the number of b1 is thefluoro-containing cyclic group, L₁ may not be a substituted orunsubstituted triazine group, when at least one of R₂(s) in the numberof b2 is the fluoro-containing cyclic group, L₂ may not be a substitutedor unsubstituted triazine group, and when at least one of R₃(s) in thenumber of b3 is the fluoro-containing cyclic group, L₃ may not be asubstituted or unsubstituted triazine group, and

the heterocyclic compound may not include a carbazole group, adibenzofuran group, a dibenzothiophene group, and/or a triphenylenegroup.

In one embodiment, the fluoro-containing cyclic group may include one tofive fluoro groups. For example, the fluoro-containing cyclic group mayinclude one, two, or five fluoro groups, but embodiments of the presentdisclosure are not limited thereto. For example, the fluoro-containingcyclic group may include two or more fluoro groups, but embodiments ofthe present disclosure are not limited thereto.

In one or more embodiments, the fluoro-containing cyclic group may be aC₃-C₆₀ carbocyclic group substituted with at least one —F. For example,the fluoro-containing cyclic group may be a C₆-C₆₀ aryl group or amonovalent non-aromatic condensed polycyclic group, each substitutedwith at least one —F, but embodiments of the present disclosure are notlimited thereto. For example, the fluoro-containing cyclic group may bea phenyl group, a naphthyl group, or a fluorenyl group, each substitutedwith —F, but embodiments of the present disclosure are not limitedthereto.

In one or more embodiments, the fluoro-containing cyclic group may beselected from groups represented by Formulae 4-1 to 4-19, butembodiments of the present disclosure are not limited thereto:

In Formulae 4-1 to 4-19,

Y₃₁ may be O, S, C(Z₃₃)(Z₃₄), N(Z₃₃), or Si(Z₃₃)(Z₃₄),

Z₃₁ to Z₃₄ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, atriazinyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₂₀ alkyl group, and —Si(Q₃₁)(Q₃₂)(Q₃),

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinylgroup, a pyrimidinyl group, a triazinyl group, a biphenyl group, aterphenyl group, and a phenyl group substituted with a C₁-C₂₀ alkylgroup,

e2 may be an integer from 0 to 2,

e3 may be an integer from 0 to 3,

e4 may be an integer from 0 to 4,

e6 may be an integer from 0 to 6, and

* indicates a binding site to a neighboring atom.

For example, the fluoro-containing cyclic group may be a grouprepresented by Formula 4-3 or 4-9, and Z₃₁ may be hydrogen, butembodiments of the present disclosure are not limited thereto.

In one embodiment, in Formula 1, i) when at least one of R₁(s) in thenumber of b1 is the fluoro-containing cyclic group, at least one ofL₁(s) in the number of a1 may be a single bond or a substituted orunsubstituted C₃-C₆₀ carbocyclic group,

ii) when at least one of R₂(s) in the number of b2 is thefluoro-containing cyclic group, at least one of L₂(s) in the number ofa2 may be a single bond or a substituted or unsubstituted C₃-C₆₀carbocyclic group,

iii) when at least one of R₃(s) in the number of b3 is thefluoro-containing cyclic group, at least one of L₃(s) in the number ofa3 may be a single bond or a substituted or unsubstituted C₃-C₆₀carbocyclic group, and

the substituent of the substituted C₃-C₆₀ carbocyclic group may beselected from a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀ alkoxy group.

For example, the substituted or unsubstituted C₃-C₆₀ carbocyclic groupmay be selected from:

a benzene group, a naphthalene group, and a fluorene group; and

a benzene group and a fluorene group, each substituted with a C₁-C₂₀alkyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, in Formula 1, i) at least one of R₁(s) inthe number of b1 may be the fluoro-containing cyclic group, and R₂(s) inthe number of b2 and R₃(s) in the number of b3 may each independently beselected from: a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, and a pyridinyl group; and a triazinyl group substitutedwith one or more phenyl groups;

ii) at least one of R₁(s) in the number of b1 and at least one of R₂(s)in the number of b2 may each be a fluoro-containing cyclic group, andR₃(s) in the number of b3 may each independently be selected from: aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, apyridinyl group, a fluorenyl group, an anthracenyl group, aphenanthrenyl group, a quinolinyl group, a phenanthrolinyl group, atriazinyl group, and a pyrimidinyl group; a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a pyridinyl group, afluorenyl group, an anthracenyl group, a phenanthrenyl group, aquinolinyl group, a phenanthrolinyl group, a triazinyl group, and apyrimidinyl group, each substituted with at least one selected from acyano group, a C₁-C₂₀ alkyl group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group,an anthracenyl group, a phenanthrenyl group, a triazinyl group, and apyrimidinyl group; and —B(Q₁)(Q₂); or

iii) at least one of R₁(s) in the number of b1, at least one of R₂(s) inthe number of b2, and at least one of R₃(s) in the number of b3 may eachbe a fluoro-containing cyclic group, and

Q₁ and Q₂ may each independently be a phenyl group substituted with oneor more C₁-C₂₀ alkyl groups.

In one or more embodiments, i) when b1 is two or more and at least oneof R₁(s) in the number of b1 is a fluoro-containing cyclic group, one ormore R₁(s) that are not the fluoro-containing cyclic group are includedbetween the fluoro-containing cyclic group and L₁, ii) when b2 is two ormore and at least one of R₂(s) in the number of b2 is afluoro-containing cyclic group, one or more R₂(s) that are not thefluoro-containing cyclic group may be included between thefluoro-containing cyclic group and L₂, and iii) when b3 is two or moreand at least one of R₃(s) in the number of b3 is a fluoro-containingcyclic group, one or more R₃(s) that are not the fluoro-containingcyclic group may be included between the fluoro-containing cyclic groupand L₃.

In one embodiment, L₁ to L₃ and R₁ to R₃ in Formula 1 may each notinclude a triazine group.

In one or more embodiments, the heterocyclic compound may include one tofive fluoro groups.

In one embodiment, the heterocyclic compound may be selected fromCompounds 1 to 90:

The heterocyclic compound includes the structure of Formula 1. While thepresent application is not limited by any particular mechanism or theoryit is believed that since the heterocyclic compound includes at leastone fluoro (fluorine) that is an element having high electronegativity,heterocyclic compound molecules form a strong dipole (e.g., eachmolecule of the heterocyclic compound may have a strong dipole moment).It is further believed, without limiting the present application, thatas a result, an interfacial vacuum level is lowered by intermolecularinterfacial dipole-dipole interaction (e.g., intermolecular interfacialdipole-dipole interaction between molecules of the heterocycliccompound), thereby facilitating electron injection. Also, it is believedthat even in an electron transport layer (ETL), electron transport isfacilitated by strong secondary bonding such as hydrogen bonding causedby unshared electrons of the fluoro element (fluorine), but the presentapplication is not limited by any particular mechanism or theory.

Also, since the heterocyclic compound does not include another triazinegroup between a terminus including the fluoro-containing cyclic groupand a triazine core, a molecular structure of the heterocyclic compoundmay be designed to be not symmetrical but asymmetrical. Accordingly, themolecules may have stronger polarity.

A synthesis method for the heterocyclic compound represented by Formula1 would be apparent to those of ordinary skill in the art by referringto the following examples.

At least one of the heterocyclic compound of Formula 1 may be usedbetween a pair of electrodes of an organic light-emitting device. Forexample, the heterocyclic compound may be included in at least one layerselected from a hole transport region, an electron transport region, andan emission layer. In one or more embodiments, the heterocyclic compoundof Formula 1 may be used as a material for a capping layer locatedoutside a pair of electrodes of an organic light-emitting device.

Accordingly, provided is an organic light-emitting device including: afirst electrode; a second electrode facing the first electrode; and anorganic layer between the first electrode and the second electrode andincluding an emission layer, wherein the organic layer includes at leastone condensed cyclic compound.

The expression “(an organic layer) includes at least one heterocycliccompound,” as used herein, may include a case in which “(an organiclayer) includes identical compounds represented by Formula 1” and a casein which “(an organic layer) includes two or more different heterocycliccompounds.”

In one embodiment, the first electrode is an anode, and the secondelectrode is a cathode, and the organic layer further a hole transportregion between the first electrode and the emission layer and anelectron transport region between the emission layer and the secondelectrode, and the hole transport region includes a hole injectionlayer, a hole transport layer, an emission auxiliary layer, an electronblocking layer, or any combination thereof, and the electron transportregion includes a buffer layer, a hole blocking layer, an electroncontrol layer, an electron transport layer, an electron injection layer,or any combination thereof.

In one embodiment, the electron transport region may include at leastone of the heterocyclic compounds disclosed herein.

In one or more embodiments, the electron transport region may include anelectron transport layer, and the electron transport layer may includethe heterocyclic compound.

In one or more embodiments, the electron transport region may include anemission auxiliary layer, and the emission auxiliary layer may includethe heterocyclic compound.

In one or more embodiments, the hole transport region may include ap-dopant, and the p-dopant may have a lowest unoccupied molecularorbital (LUMO) energy level of about −3.5 eV or less.

In one or more embodiments, the p-dopant may include a cyanogroup-containing compound.

The host in the emission layer may include at least one selected from ananthracene-based compound, a pyrene-based compound, and aspiro-bifluorene-based compound, but embodiments of the presentdisclosure are not limited thereto.

The dopant in the emission layer may include at least one selected froma styryl-based compound and an amine-based compound, but embodiments ofthe present disclosure are not limited thereto.

In the organic light-emitting device, the emission layer may be a firstemission layer for emitting first color light,

between the first electrode and second electrode, i) at least one secondemission layer for emitting second color light may be further included,and ii) at least one second emission layer for emitting second colorlight and at least one third emission layer for emitting third colorlight may be further included,

a maximum (e.g., an upper end) emission wavelength of the first colorlight, a maximum (e.g., an upper end) emission wavelength of the secondcolor light, and a maximum (e.g., an upper end) emission wavelength ofthe third color light may be identical to or different from each other,and

the first color light and the second color light may be emitted in theform of mixed light, or the first color light, the second color light,and the third color light may be emitted in the form of mixed light.

The organic light-emitting device may further include at least oneselected from a first capping layer disposed in a pathway along whichlight generated in an emission layer proceeds toward the outside throughthe first electrode and a second capping layer disposed in a pathwayalong which light generated in an emission layer proceeds toward theoutside through the second electrode, and the at least one selected fromthe first capping layer and the second capping layer may include atleast one heterocyclic compound represented by Formula 1.

For example, the organic light-emitting device may have i) a stackedstructure including a first electrode, an organic layer, a secondelectrode, and a second capping layer which are sequentially stacked inthis stated order, ii) a stacked structure including a first cappinglayer, a first electrode, an organic layer, and a second electrode whichare sequentially stacked in this stated order, or iii) a stackedstructure including a first capping layer, a first electrode, an organiclayer, a second electrode, and a second capping layer which aresequentially stacked in this stated order, and at least one selectedfrom the first capping layer and the second capping layer may includethe heterocyclic compound.

The term “organic layer,” as used herein, refers to a single layerand/or a plurality of layers disposed between the first electrode andthe second electrode of the organic light-emitting device. A materialincluded in the “organic layer” is not limited to an organic material.

Description of FIG. 1

FIG. 1 is a schematic view of an organic light-emitting device 10according to an embodiment. The organic light-emitting device 10includes a first electrode 110, an organic layer 150, and a secondelectrode 190.

Hereinafter, the structure of the organic light-emitting device 10according to an embodiment and a method of manufacturing the organiclight-emitting device 10 will be described in connection with FIG. 1 .

[First Electrode 110]

In FIG. 1 , a substrate may be additionally disposed under the firstelectrode 110 or above the second electrode 190. The substrate may be aglass substrate or a plastic substrate, each having excellent mechanicalstrength, thermal stability, transparency, surface smoothness, ease ofhandling, and water resistance.

The first electrode 110 may be formed by depositing or sputtering amaterial for forming the first electrode 110 on the substrate. When thefirst electrode 110 is an anode, the material for a first electrode maybe selected from materials having a high work function to facilitatehole injection.

The first electrode 110 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode. When the firstelectrode 110 is a transmissive electrode, a material for forming afirst electrode may be selected from indium tin oxide (ITO), indium zincoxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), and any combinationsthereof, but embodiments of the present disclosure are not limitedthereto. In one or more embodiments, when the first electrode 110 is asemi-transmissive electrode or a reflectable (reflective) electrode, amaterial for forming a first electrode may be selected from magnesium(Mg), silver (Ag), aluminum (AI), aluminum-lithium (Al—Li), calcium(Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and anycombinations thereof, but embodiments of the present disclosure are notlimited thereto.

The first electrode 110 may have a single-layered structure, or amulti-layered structure including two or more layers. For example, thefirst electrode 110 may have a three-layered structure of ITO/Ag/ITO,but the structure of the first electrode 110 is not limited thereto.

[Organic Layer 150]

The organic layer 150 is disposed on the first electrode 110. Theorganic layer 150 may include an emission layer.

The organic layer 150 may further include a hole transport regionbetween the first electrode 110 and the emission layer, and an electrontransport region between the emission layer and the second electrode190.

[Hole Transport Region in Organic Layer 150]

The hole transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The hole transport region may include at least one layer selected from ahole injection layer, a hole transport layer, an emission auxiliarylayer, and an electron blocking layer.

For example, the hole transport region may have a single-layeredstructure including a single layer including a plurality of differentmaterials, or a multi-layered structure having a hole injectionlayer/hole transport layer structure, a hole injection layer/holetransport layer/emission auxiliary layer structure, a hole injectionlayer/emission auxiliary layer structure, a hole transportlayer/emission auxiliary layer structure, or a hole injection layer/holetransport layer/electron blocking layer structure, wherein for eachstructure, constituting layers are sequentially stacked from the firstelectrode 110 in this stated order, but the structure of the holetransport region is not limited thereto.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound representedby Formula 201, and a compound represented by Formula 202:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

L₂₀₅ may be selected from *—O—*′, *—S—*′, *—N(Q₂₀₁)-*′, a substituted orunsubstituted C₁-C₂₀ alkylene group, a substituted or unsubstitutedC₂-C₂₀ alkenylene group, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xa1 to xa4 may each independently be an integer from 0 to 3,

xa5 may be an integer from 1 to 10, and

R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independently be selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 202, R₂₀₁ and R₂₀₂ may optionally be linked viaa single bond, a dimethyl-methylene group, or a diphenyl-methylenegroup, and R₂₀₃ and R₂₀₄ may optionally be linked via a single bond, adimethyl-methylene group, or a diphenyl-methylene group.

In one embodiment, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may each independently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, xa1 to xa4 may each independently be 0, 1,or 2.

In one or more embodiments, xa5 may be 1, 2, 3, or 4.

In one or more embodiments, R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independentlybe selected from:

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described elsewhere herein.

In one or more embodiments, at least one selected from R₂₀₁ to R₂₀₃ inFormula 201 may independently be selected from:

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a phenyl group substituted with a C₁-C₁₀ alkylgroup, a phenyl group substituted with —F, a naphthyl group, a fluorenylgroup, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, in Formula 202, i) R₂₀₁ and R₂₀₂ may belinked via a single bond, and/or ii) R₂₀₃ and R₂₀₄ may be linked via asingle bond.

In one or more embodiments, at least one selected from R₂₀₁ to R₂₀₄ inFormula 202 may each independently be selected from:

a carbazolyl group; and

a carbazolyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, acarbazolyl group, a dibenzofuranyl group, and a dibenzothlophenyl group,

but embodiments of the present disclosure are not limited thereto.

The compound represented by Formula 201 may be represented by Formula201A:

In one embodiment, the compound represented by Formula 201 may berepresented by Formula 201A(1) below, but embodiments of the presentdisclosure are not limited thereto:

In one embodiment, the compound represented by Formula 201 may berepresented by Formula 201A-1 below, but embodiments of the presentdisclosure are not limited thereto:

In one embodiment, the compound represented by Formula 202 may berepresented by Formula 202A:

In one embodiment, the compound represented by Formula 202 may berepresented by Formula 202A-1:

In Formulae 201A, 201A(1), 201A-1, 202A, and 202A-1,

L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂ to R₂₀₄ are the same asdescribed above,

R₂₁₁ and R₂₁₂ may be understood by referring to the description providedherein in connection with R₂₀₃, and

R₂₁₃ to R₂₁₇ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group.

The hole transport region may include at least one compound selectedfrom Compounds HT1 to HT39, but embodiments of the present disclosureare not limited thereto:

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When thehole transport region includes at least one selected from a holeinjection layer and a hole transport layer, the thickness of the holeinjection layer may be in a range of about 100 Å to about 9,000 Å, andfor example, about 100 Å to about 1,000 Å, and the thickness of the holetransport layer may be in a range of about 50 Å to about 2,000 Å, andfor example, about 100 Å to about 1500 Å. When the thicknesses of thehole transport region, the hole injection layer, and the hole transportlayer are within these ranges, suitable or satisfactory holetransporting characteristics may be obtained without a substantialincrease in driving voltage.

The emission auxiliary layer may increase light-emission efficiency bycompensating for an optical resonance distance according to thewavelength of light emitted by an emission layer, and the electronblocking layer may block the flow of electrons from an electrontransport region. The emission auxiliary layer and the electron blockinglayer may include the materials as described above.

[p-Dopant]

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant.

In one embodiment, the p-dopant may have a LUMO of about −3.5 eV orless.

The p-dopant may include at least one selected from a quinonederivative, a metal oxide, and a cyano group-containing compound, butembodiments of the present disclosure are not limited thereto.

For example, the p-dopant may include at least one selected from:

a quinone derivative, such as tetracyanoquinodimethane (TCNQ) or2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

a metal oxide, such as tungsten oxide or molybdenum oxide;

1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

a compound represented by Formula 221 below:

but embodiments of the present disclosure are not limited thereto:

In Formula 221,

R₂₂₁ to R₂₂₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, provided that at leastone selected from R₂₂₁ to R₂₂₃ has at least one substituent selectedfrom a cyano group, —F, —Cl, —Br, —I, a C₁-C₂₀ alkyl group substitutedwith —F, a C₁-C₂₀ alkyl group substituted with —Cl, a C₁-C₂₀ alkyl groupsubstituted with —Br, and a C₁-C₂₀ alkyl group substituted with —I.

[Emission Layer in Organic Layer 150]

When the organic light-emitting device 10 is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, or a blue emission layer,according to a sub-pixel. In one or more embodiments, the emission layermay have a stacked structure of two or more layers selected from a redemission layer, a green emission layer, and a blue emission layer, inwhich the two or more layers contact each other or are separated fromeach other. In one or more embodiments, the emission layer may includetwo or more materials selected from a red light-emitting material, agreen light-emitting material, and a blue light-emitting material, inwhich the two or more materials are mixed with each other in a singlelayer to emit white light.

The emission layer may include a host and a dopant. The dopant mayinclude at least one selected from a phosphorescent dopant and afluorescent dopant.

An amount of the dopant in the emission layer may be in a range of about0.01 parts by weight to about 15 parts by weight based on 100 parts byweight of the host, but embodiments of the present disclosure are notlimited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within this range, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

[Host in Emission Layer]

In one or more embodiments, the host may further include a compoundrepresented by Formula 301 below:[Ar₃₀₁]_(xb11)-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb21).  Formula 301

In Formula 301,

Ar₃₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₃-C₆₀ heterocyclic group,

xb11 may be 1, 2, or 3,

L₃₀₁ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group;

xb1 may be an integer from 0 to 5,

R₃₀₁ may be selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₆₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂),—B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), and —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer from 1 to 5, and

Q₃₀₁ to Q₃₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group, but embodiments of the presentdisclosure are not limited thereto.

In one embodiment, in Formula 301, Ar₃₀₁ may be selected from:

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup; and

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, —Si(Q₃₁)(Q₃)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group, but embodiments of the present disclosureare not limited thereto.

In Formula 301, xb11 may be two or more, and two or more of Ar₃₀₁(s) maybe linked via a single bond.

In one or more embodiments, the compound represented by Formula 301 maybe represented by Formula 301-1 or 301-2:

In Formulae 301-1 and 301-2,

A₃₀₁ to A₃₀₄ may each independently be selected from a benzene group, anaphthalene group, a phenanthrene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a pyridine group,a pyrimidine group, an indene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,an indole group, a carbazole group, a benzocarbazole group, adibenzocarbazole group, a furan group, a benzofuran group, adibenzofuran group, a naphthofuran group, a benzonaphthofuran group, adinaphthofuran group, a thiophene group, a benzothiophene group, adibenzothiophene group, a naphthothiophene group, abenzonaphthothiophene group, and a dinaphthothiophene group,

X₃₀₁ may be O, S, or N-[(L₃₀₄)_(xb4)-R₃₀₄],

R₃₁₁ to R₃₁₄ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁) and —P(═O)(Q₃₁)(Q₃₂),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, R₃₀₁, and Q₃₁ to Q₃₃ may each independently be the same asdescribed above,

L₃₀₂ to L₃₀₄ may each independently be the same as described inconnection with L₃₀₁,

xb2 to xb4 may each independently be the same as described in connectionwith xb1, and

R₃₀₂ to R₃₀₄ may each independently be the same as described inconnection with R₃₀₁.

For example, in Formulae 301, 301-1, and 301-2, L₃₀₁ to L₃₀₄ may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may be the same as described above.

In one embodiment, in Formulae 301, 301-1, and 301-2, R₃₀₁ to R₃₀₄ mayeach independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may be the same as described above.

In one or more embodiments, the host may include an alkaline earth metalcomplex. For example, the host may be selected from a Be complex (forexample, Compound H55), a Mg complex, and a Zn complex.

The host may include at least one selected from9,10-di(2-naphthyl)anthracene (ADN),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene(mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds H1 to H55,but embodiments of the present disclosure are not limited thereto:

[Phosphorescent Dopant Included in Emission Layer in Organic Layer 150]

The phosphorescent dopant may include an organometallic complexrepresented by Formula 401 below:M(L₄₀₁)_(xc1)(L₄₀₂)_(xc2)  Formula 401

In Formulae 401 and 402,

M may be selected from iridium (Ir), platinum (Pt), palladium (Pd),osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu),terbium (Tb), rhodium (Rh), and thulium (Tm),

L₄₀₁ may be selected from ligands represented by Formula 402, and xc1may be 1, 2, or 3, wherein, when xc1 is two or more, two or more L₄₀₁(s)may be identical to or different from each other,

L₄₀₂ may be an organic ligand, and xc2 may be an integer from 0 to 4,wherein, when xc2 is two or more, two or more L₄₀₂(s) may be identicalto or different from each other,

X₄₀₁ to X₄₀₄ may each independently be nitrogen or carbon,

X₄₀₁ and X₄₀₃ may be linked via a single bond or a double bond, and X₄₀₂and X₄₀₄ may be linked via a single bond or a double bond,

A₄₀₁ and A₄₀₂ may each independently be selected from a C₅-C₆₀carbocyclic group or a C₁-C₆₀ heterocyclic group,

X₄₀₅ may be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₁)-*′,*—C(Q₄₁₁)(Q₄₁₂)-*′, *—C(Q₄₁₁)═C(Q₄₁₂)-*′, *—C(Q₄₁₁)=*′, or *═C═*′, andQ₄₁₁ and Q₄₁₂ may each independently be hydrogen, deuterium, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, or a naphthyl group,

X₄₀₆ may be a single bond, O, or S,

R₄₀₁ and R₄₀₂ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₁-C₂₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₆₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₄₀₁)(Q₄₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂),—B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂),

Q₄₀₁ to Q₄₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a C₆-C₂₀ aryl group, and a C₁-C₂₀heteroaryl group,

xc11 and xc12 may each independently be an integer from 0 to 10, and

* and *′ in Formula 402 each indicate a binding site to M in Formula401.

In one embodiment, A₄₀₁ and A₄₀₂ in Formula 402 may each independentlybe selected from a benzene group, a naphthalene group, a fluorene group,a spiro-bifluorene group, an indene group, a pyrrole group, a thiophenegroup, a furan group, an imidazole group, a pyrazole group, a thiazolegroup, an isothiazole group, an oxazole group, an isoxazole group, apyridine group, a pyrazine group, a pyrimidine group, a pyridazinegroup, a quinoline group, an isoquinoline group, a benzoquinoline group,a quinoxaline group, a quinazoline group, a carbazole group, abenzimidazole group, a benzofuran group, a benzothiophene group, anisobenzothiophene group, a benzoxazole group, an isobenzoxazole group, atriazole group, a tetrazole group, an oxadiazole group, a triazinegroup, a dibenzofuran group, and a dibenzothiophene group.

In one or more embodiments, in Formula 402, i) X₄₀₁ may be nitrogen, andX₄₀₂ may be carbon, or ii) X₄₀₁ and X₄₀₂ may each be nitrogen at thesame time.

In one or more embodiments, R₄₀₂ and R₄₀₂ in Formula 401 may eachindependently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a phenyl group, a naphthyl group, a cyclopentyl group,a cyclohexyl group, an adamantanyl group, a norbomanyl group, and anorbomenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbomanyl group, a norbomenyl group, a phenyl group, a biphenyl group,a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbomanyl group, a norbomenyl group a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and adibenzothiophenyl group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, an adamantanyl group, a norbomanyl group, a norbomenylgroup, a phenyl group, a biphenyl group, a terphenyl group, a naphthylgroup, a fluorenyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, an isoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a carbazolyl group, a dibenzofuranyl group, and adibenzothiophenyl group; and

—Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀),—S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂), and

Q₄₀₁ to Q₄₀₃ may each independently be selected from a C₁-C₆₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, and anaphthyl group, but are not limited thereto.

In one or more embodiments, when xc1 in Formula 401 is two or more, twoA₄₀₁ (s) in two or more L₄₀₁ (s) may optionally be linked via X₄₀₇,which is a linking group, or two A₄₀₂(s) in two or more L₄₀₁(s) mayoptionally be linked via X₄₀₈, which is a linking group (see CompoundsPD1 to PD4 and PD7). X₄₀₇ and X₄₀₈ may each independently be a singlebond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₃)-*′, *C(Q₄₁₃)(Q₄₁₄)-*, or*—C(Q₄₁₃)=C(Q₄₁₄)-*′ (wherein Q₄₁₃ and Q₄₁₄ may each independently behydrogen, deuterium, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, or a naphthyl group),but embodiments of the present disclosure are not limited thereto.

L₄₀₂ in Formula 401 may be a monovalent, divalent, or trivalent organicligand. For example, L₄₀₂ may be selected from a halogen, a diketone(for example, acetylacetonate), a carboxylic acid (for example,picolinate), —C(═O), an isonitrile, —CN, and a phosphorus-containingmaterial (for example, phosphine or phosphite), but embodiments of thepresent disclosure are not limited thereto.

In one or more embodiments, the phosphorescent dopant may be selectedfrom, for example, Compounds PD1 to PD25, but embodiments of the presentdisclosure arm not limited thereto:

[Fluorescent Dopant in Emission Layer]

The fluorescent dopant may include an arylamine compound or astyrylamine compound.

The fluorescent dopant may include a compound represented by Formula 501below:

In Formula 501,

Ar₅₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

L₅₀₁ to L₅₀₃ may each independently be selected from a substituted orunsubstituted C₃-C₆₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xd1 to xd3 may each independently be an integer of 0 to 3,

R₅₀₁ and R₅₀₂ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₈₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,and

xd4 may be an integer of 1 to 6.

In one embodiment, Ar₅₀₁ in Formula 501 may be selected from:

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup; and

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, L₅₀₁ to L₅₀₃ in Formula 501 may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group.

In one or more embodiments, R₅₀₁ and R₅₀₂ in Formula 501 may eachindependently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₂₀ alkyl group, a C₇-C₂₀ alkoxy group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, xd4 in Formula 501 may be 2, but embodimentsof the present disclosure are not limited thereto.

For example, the fluorescent dopant may be selected from Compounds FD1to FD22:

In one or more embodiments, the fluorescent dopant may be selected fromthe following compounds, but embodiments of the present disclosure arenot limited thereto:

[Electron Transport Region in Organic Layer 150]

The electron transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron transport region may include at least one selected from abuffer layer, a hole blocking layer, an electron control layer, anelectron transport layer, and an electron injection layer, butembodiments of the present disclosure are not limited thereto.

For example, the electron transport region may have an electrontransport layer/electron injection layer structure, a hole blockinglayer/electron transport layer/electron injection layer structure, anelectron control layer/electron transport layer/electron injection layerstructure, or a buffer layer/electron transport layer/electron injectionlayer structure, wherein for each structure, constituting layers aresequentially stacked from an emission layer. However, embodiments of thestructure of the electron transport region are not limited thereto.

The electron transport region may include a compound represented byFormula 1.

In one embodiment, the electron transport region (for example, a bufferlayer, a hole blocking layer, an electron control layer, or an electrontransport layer in the electron transport region) may include ametal-free compound containing at least one π electron-depletednitrogen-containing ring.

The term “π electron-depleted nitrogen-containing ring,” as used herein,indicates a C₁-C₆₀ heterocyclic group having at least one *—N═*′ moietyas a ring-forming moiety.

For example, the “π electron-depleted nitrogen-containing ring” may bei) at least one selected from a 6-membered to 7-memberedheteromonocyclic group having at least one *—N═*′ moiety, ii) aheteropolycyclic group in which two or more selected from 5-membered to7-membered heteromonocyclic groups each having at least one *—N=*′moiety are condensed with each other (e.g., combined together), or iii)a heteropolycyclic group in which at least one selected from 5-memberedto 7-membered heteromonocyclic groups, each having at least one *—N=*′moiety, is condensed with (e.g., combined with) at least one C₅-C₆₀carbocyclic group.

Examples of the π electron-depleted nitrogen-containing ring Include animidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, anisoxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, anindazole, a purine, a quinoline, an isoquinoline, a benzoquinoline, aphthalazine, a naphthyridine, a quinoxaline, a quinazoline, a cinnoline,a phenanthridine, an acridine, a phenanthroline, a phenazine, abenzimidazole, an isobenzothiazole, a benzoxazole, an isobenzoxazole, atriazole, a tetrazole, an oxadiazole, a triazine, thiadiazol, animidazopyridine, an imidazopyrimidine, and an azacarbazole, but are notlimited thereto.

For example, the electron transport region may include a compoundrepresented by Formula 601:[Ar₆₀₁]_(xe11)-[(L₆₀₁)_(xe1)-R₆₀₁]_(xe21).  Formula 601

In Formula 601,

Ar₆₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xe11 may be 1, 2, or 3,

L₆₀₁ may be selected from a substituted or unsubstituted C₃-C₆₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xe1 may be an integer from 0 to 5,

R₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group,a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁),—S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁ to Q₆₀₃ may each independently be a C₁-C₆₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or anaphthyl group, and

xe21 may be an integer from 1 to 5.

In one embodiment, at least one of Ar₆₀₁(s) in the number of xe11 andR₆₀₁(s) in the number of xe21 may include the π electron-depletednitrogen-containing ring.

In one embodiment, ring Ar₆₀₁ in Formula 601 may be selected from:

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an iso-benzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group; and

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an iso-benzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

When xe11 in Formula 601 is two or more, two or more Ar₆₀₁(s) may belinked via a single bond.

In one or more embodiments, Ar₆₀₁ in Formula 601 may be an anthracenegroup.

In one or more embodiments, a compound represented by Formula 601 may berepresented by Formula 601-1:

In Formula 601-1,

X₆₁₄ may be N or C(R₆₁₄), X₆₁₅ may be N or C(R₆₁₅), X₆₁₆ may be N orC(R₆₁₆), and at least one selected from X₆₁₄ to X₆₁₆ may be N,

L₆₁₁ to L₆₁₃ may each independently be the same as described inconnection with L₆₀₁,

xe611 to xe613 may each independently be the same as described inconnection with xe1,

R₆₁₁ to R₆₁₃ may each independently be the same as described inconnection with R₆₀₁, and

R₆₁₄ to R₆₁₆ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

In one embodiment, L₆₀₁ and L₆₁₁ to L₆₁₃ in Formulae 601 and 601-1 mayeach independently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, and an azacarbazolyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and601-1 may each independently be 0, 1, or 2.

In one or more embodiments, in Formulae 601 and 601-1, R₆₀₁ and R₆₁₁ toR₆₁₃ may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

—S(═O)₂(Q₆₀₁) and —P(═O)(Q₆₀₁)(Q₆₀₂), and

Q₆₀₁ and Q₆₀₂ may be the same as described above.

The electron transport region may include at least one compound selectedfrom Compounds ET1 to ET36, but embodiments of the present disclosureare not limited thereto:

In one or more embodiments, the electron transport region may include atleast one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline(BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq₃, BAlq,3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), and NTAZ:

Thicknesses of the buffer layer, the hole blocking layer, and theelectron control layer may each be in a range of about 20 Å to about1,000 Å, for example, about 30 Å to about 300 Å. When the thicknesses ofthe buffer layer, the hole blocking layer, and the electron controllayer are within these ranges, the electron blocking layer may haveexcellent electron blocking characteristics or electron controlcharacteristics without a substantial increase in driving voltage.

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within the rangedescribed above, the electron transport layer may have suitable orsatisfactory electron transport characteristics without a substantialincrease in driving voltage.

The electron transport region (for example, the electron transport layerin the electron transport region) may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include at least one selected fromalkali metal complex and alkaline earth-metal complex. The alkali metalcomplex may include a metal ion selected from a Li ion, a Na ion, a Kion, a Rb ion, and a Cs ion, and the alkaline earth-metal complex mayinclude a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Srion, and a Ba ion. A ligand coordinated with the metal ion of the alkalimetal complex or the alkaline earth-metal complex may be selected from ahydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, ahydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, ahydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxydiphenyithiadiazol, a hydroxy phenylpyridine, a hydroxyphenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, aphenanthroline, and a cyclopentadiene, but embodiments of the presentdisclosure are not limited thereto.

For example, the metal-containing material may include a Li complex. TheLi complex may include, for example, Compound ET-D1 (lithium quinolate,LIQ) or ET-D2:

The electron transport region may include an electron injection layerthat facilitates injection of electrons from the second electrode 190.The electron injection layer may directly contact the second electrode190.

The electron injection layer may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron injection layer may include an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof.

The alkali metal may be selected from Li, Na, K, Rb, and Cs. In oneembodiment, the alkali metal may be Li, Na, or Cs. In one or moreembodiments, the alkali metal may be Li or Cs, but embodiments of thepresent disclosure are not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

The alkali metal compound, the alkaline earth-metal compound, and therare earth metal compound may be selected from oxides and halides (forexample, fluorides, chlorides, bromides, or iodides) of the alkalimetal, the alkaline earth-metal, and the rare earth metal.

The alkali metal compound may be selected from alkali metal oxides, suchas Li₂O, Cs₂O, or K₂O, and alkali metal halides, such as LiF, NaF, CsF,KF, LiI, NaI, CsI, or KI. In one embodiment, the alkali metal compoundmay be selected from LiF, Li₂O, NaF, LiI, NaI, CsI, and KI, butembodiments of the present disclosure are not limited thereto.

The alkaline earth metal compound may be selected from BaO, SrO, CaO,Ba_(x)Sr_(1-x)O (0<x<1), and Ba_(x)Ca_(1-x)O (0<x<1). In one embodiment,the alkaline earth metal compound may be selected from BaO, SrO, andCaO, but embodiments of the present disclosure are not limited thereto.

The rare earth metal compound may be selected from YbF₃, ScF₃, ScO₃,Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. In one embodiment, the rare earth metalcompound may be selected from YbF₃, ScF₃, TbF₃, YbI₃, ScI₃, and TbI₃,but embodiments of the present disclosure are not limited thereto.

The alkali metal complex, the alkaline earth-metal complex, and the rareearth metal complex may include an ion of alkali metal, alkalineearth-metal, and rare earth metal as described above, and a ligandcoordinated with a metal ion of the alkali metal complex, the alkalineearth-metal complex, or the rare earth metal complex may be selectedfrom hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline,hydroxy acridine, hydroxy phenanthridine, hydroxy phenyl oxazole,hydroxy phenylthiazole, hydroxy diphenyl oxadiazole, hydroxydiphenyithiadiazol, hydroxy phenylpyridine, hydroxy phenylbenzimidazole,hydroxy phenylbenzothiazole, bipyridine, phenanthroline, andcyclopentadiene, but embodiments of the present disclosure are notlimited thereto.

The electron injection layer may consist of an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof, as described above. In one or moreembodiments, the electron injection layer may further include an organicmaterial. When the electron injection layer further includes an organicmaterial, an alkali metal, an alkaline earth metal, a rare earth metal,an alkali metal compound, an alkaline earth-metal compound, a rare earthmetal compound, an alkali metal complex, an alkaline earth-metalcomplex, a rare earth metal complex, or any combinations thereof may behomogeneously or non-homogeneously dispersed in a matrix including theorganic material.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within the range describedabove, the electron injection layer may have suitable or satisfactoryelectron injection characteristics without a substantial increase indriving voltage.

[Second Electrode 190]

The second electrode 190 may be disposed on the organic layer 150 havingsuch a structure. The second electrode 190 may be a cathode which is anelectron injection electrode, and in this regard, a material for formingthe second electrode 190 may be selected from metal, an alloy, anelectrically conductive compound, and a combination thereof, which havea relatively low work function.

The second electrode 190 may include at least one selected from lithium(Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver(Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are notlimited thereto. The second electrode 190 may be a transmissiveelectrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 190 may have a single-layered structure, or amulti-layered structure including two or more layers.

Description of FIGS. 2 to 4

An organic light-emitting device 20 of FIG. 2 includes a first cappinglayer 210, a first electrode 110, an organic layer 150, and a secondelectrode 190 which are sequentially stacked in this stated order, anorganic light-emitting device 30 of FIG. 3 includes a first electrode110, an organic layer 150, a second electrode 190, and a second cappinglayer 220 which are sequentially stacked in this stated order, and anorganic light-emitting device 40 of FIG. 4 includes a first cappinglayer 210, a first electrode 110, an organic layer 150, a secondelectrode 190, and a second capping layer 220.

Regarding FIGS. 2 to 4 , the first electrode 110, the organic layer 150,and the second electrode 190 may be understood by referring to thedescription presented in connection with FIG. 1 .

In the organic layer 150 of each of the organic light-emitting devices20 and 40, light generated in an emission layer may pass through thefirst electrode 110, which is a semi-transmissive electrode or atransmissive electrode, and the first capping layer 210 toward theoutside, and in the organic layer 150 of each of the organiclight-emitting devices 30 and 40, light generated in an emission layermay pass through the second electrode 190, which is a semi-transmissiveelectrode or a transmissive electrode, and the second capping layer 220toward the outside.

The first capping layer 210 and the second capping layer 220 mayincrease external luminescent efficiency according to the principle ofconstructive interference.

The first capping layer 210 and the second capping layer 220 may eachindependently be an organic capping layer including an organic material,an inorganic capping layer including an inorganic material, or acomposite capping layer including an organic material and an inorganicmaterial.

At least one selected from the first capping layer 210 and the secondcapping layer 220 may each independently include at least one materialselected from carbocyclic compounds, heterocyclic compounds, amine-basedcompounds, porphyrine derivatives, phthalocyanine derivatives,naphthalocyanine derivatives, alkali metal complexes, and alkalineearth-based complexes. The carbocyclic compound, the heterocycliccompound, and the amine-based compound may be optionally substitutedwith a substituent containing at least one element selected from O, N,S, Se, Si, F, Cl, Br, and I.

In one embodiment, at least one selected from the first capping layer210 and the second capping layer 220 may each independently include anamine-based compound.

In one embodiment, at least one selected from the first capping layer210 and the second capping layer 220 may each independently include thecompound represented by Formula 201 or the compound represented byFormula 202.

In one or more embodiments, at least one selected from the first cappinglayer 210 and the second capping layer 220 may each independentlyinclude a compound selected from Compounds HT28 to HT33 (shown elsewhereherein) and Compounds CP1 to CP5, but embodiments of the presentdisclosure are not limited thereto;

Hereinbefore, the organic light-emitting device according to anembodiment has been described in connection with FIGS. 1 to 4 . However,embodiments of the present disclosure are not limited thereto.

Layers constituting the hole transport region, an emission layer, andlayers constituting the electron transport region may be formed in acertain region by using one or more suitable methods selected fromvacuum deposition, spin coating, casting, Langmuir-Blodgett (LB)deposition, ink-jet printing, laser-printing, and laser-induced thermalimaging.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed byvacuum deposition, the vacuum deposition may be performed at adeposition temperature of about 100° C. to about 500° C., at a vacuumdegree of about 10⁻⁸ to torr to about 10⁻³ torr, and at a depositionspeed of about 0.01 Å/sec to about 100 Å/sec by taking into account amaterial to be included in a layer to be formed, and the structure of alayer to be formed.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed by spincoating, the spin coating may be performed at a coating speed of about2,000 rpm to about 5,000 rpm and at a heat treatment temperature ofabout 80° C. to 200° C. by taking into account a material to be includedin a layer to be formed, and the structure of a layer to be formed.

[General Definition of Substituents]

The term “C₁-C₆₀ alkyl group,” as used herein, refers to a linear orbranched aliphatic saturated hydrocarbon monovalent group having 1 to 60carbon atoms, and examples thereof include a methyl group, an ethylgroup, a propyl group, an isobutyl group, a sec-butyl group, atert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group.The term “C₁-C₆₀ alkylene group,” as used herein, refers to a divalentgroup having substantially the same structure as the C₁-C₆₀ alkyl group,except that the C₁-C₆₀ alkylene group is divalent instead of monovalent.

The term “C₂-C₆₀ alkenyl group,” as used herein, refers to a hydrocarbongroup having at least one carbon-carbon double bond at a main chain(e.g., in the middle) or at a terminus of the C₂-C₆₀ alkyl group, andexamples thereof include an ethenyl group, a propenyl group, and abutenyl group. The term “C₂-C₆₀ alkenylene group,” as used herein,refers to a divalent group having substantially the same structure asthe C₂-C₆₀ alkenyl group, except that the C₂-C₆₀ alkenylene group isdivalent instead of monovalent.

The term “C₂-C₆₀ alkynyl group,” as used herein, refers to a hydrocarbongroup having at least one carbon-carbon triple bond at a main chain(e.g., in the middle) or at a terminus of the C₂-C₆₀ alkyl group, andexamples thereof include an ethynyl group, and a propynyl group. Theterm “C₂-C₆₀ alkynylene group,” as used herein, refers to a divalentgroup having substantially the same structure as the C₂-C₆₀ alkynylgroup, except that the C₂-C₆₀ alkynylene group is divalent instead ofmonovalent.

The term “C₁-C₆₀ alkoxy group,” as used herein, refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and examples thereof include a methoxy group, an ethoxy group, and anisopropyloxy group.

The term “C₃-C₁₀ cycloalkyl group,” as used herein, refers to amonovalent saturated hydrocarbon monocyclic group having 3 to 10 carbonatoms, and examples thereof include a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.The term “C₃-C₁₀ cycloalkylene group,” as used herein, refers to adivalent group having substantially the same structure as the C₃-C₁₀cycloalkyl group, except that the C₃-C₁₀ cycloalkylene group is divalentinstead of monovalent.

The term “C₁-C₁₀ heterocycloalkyl group,” as used herein, refers to amonovalent monocyclic group having at least one heteroatom selected fromN, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms, andexamples thereof include a 1,2,3,4-oxatriazolidinyl group, atetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term“C₁-C₁₀ heterocycloalkylene group,” as used herein, refers to a divalentgroup having substantially the same structure as the C₁-C₁₀heterocycloalkyl group, except that the C₁-C₁₀ heterocycloalkylene groupis divalent instead of monovalent.

The term “C₃-C₁₀ cycloalkenyl group,” as used herein, refers to amonovalent monocyclic group that has 3 to 10 carbon atoms and at leastone carbon-carbon double bond in the ring thereof and no aromaticity(e.g., the monocyclic group is not aromatic), and examples thereofinclude a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenylgroup. The term “C₃-C₁₀ cycloalkenylene group,” as used herein, refersto a divalent group having substantially the same structure as theC₃-C₁₀ cycloalkenyl group, except that the C₃-C₁₀ cycloalkenylene groupis divalent instead of monovalent.

The term “C₁-C₁₀ heterocycloalkenyl group,” as used herein, refers to amonovalent monocyclic group that has at least one heteroatom selectedfrom N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms,and at least one carbon-carbon double bond in its ring. Non-limitingexamples of the C₁-C₁₀ heterocycloalkenyl group include a4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, anda 2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup,” as used herein, refers to a divalent group having substantiallythe same structure as the C₁-C₁₀ heterocycloalkenyl group, except thatthe C₁-C₁₀ heterocycloalkenylene group is divalent instead ofmonovalent.

The term “C₆-C₈ aryl group,” as used herein, refers to a monovalentgroup having a carbocyclic aromatic system having 6 to 60 carbon atoms,and a C₆-C₆₀ arylene group used herein refers to a divalent group havinga carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limitingexamples of the C₆-C₆₀ aryl group include a phenyl group, a naphthylgroup, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, anda chrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylenegroup each include two or more rings, the rings may be fused to eachother (e.g., combined together).

The term “C₁-C₆₀ heteroaryl group,” as used herein, refers to amonovalent group having a carbocyclic aromatic system that has at leastone heteroatom selected from N, O, Si, P, and S as a ring-forming atom,in addition to 1 to 60 carbon atoms. The term “C₁-C₆₀ heteroarylenegroup,” as used herein, refers to a divalent group having a carbocyclicaromatic system that has at least one heteroatom selected from N, O, Si,P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms.Non-limiting examples of the C₁-C₆₀ heteroaryl group include a pyridinylgroup, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, and an isoquinolinyl group. Whenthe C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylene group eachinclude two or more rings, the rings may be condensed with each other(e.g., combined together).

The term “C₆-C₆₀ aryloxy group,” as used herein, refers to —OA₁₀₂(wherein A₁₀₂ is the C₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio groupused herein indicates —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

The term “monovalent non-aromatic condensed polycyclic group,” as usedherein, refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed with each other (e.g.,combined together), only carbon atoms as ring-forming atoms, and noaromaticity in its entire molecular structure (e.g., the entire moleculeis not aromatic). A detailed example of the monovalent non-aromaticcondensed polycyclic group is a fluorenyl group. The term “divalentnon-aromatic condensed polycyclic group,” used herein, refers to adivalent group having substantially the same structure as the monovalentnon-aromatic condensed polycyclic group, except that the divalentnon-aromatic condensed polycyclic group is divalent instead ofmonovalent.

The term “monovalent non-aromatic condensed heteropolycyclic group,” asused herein, refers to a monovalent group (for example, having 1 to 60carbon atoms) having two or more rings condensed to each other (e.g.,combined together), at least one heteroatom selected from N, O, Si, P,and S, other than carbon atoms, as a ring-forming atom, and noaromaticity in its entire molecular structure (e.g., the entire moleculeis not aromatic). An example of the monovalent non-aromatic condensedheteropolycyclic group is a carbazolyl group. The term “divalentnon-aromatic condensed heteropolycyclic group,” as used herein, refersto a divalent group having substantially the same structure as themonovalent non-aromatic condensed heteropolycyclic group, except thatthe divalent non-aromatic condensed heteropolycyclic group is divalentinstead of monovalent.

The term “C₅-C₆₀ carbocyclic group,” as used herein, refers to amonocyclic or polycyclic group having 5 to 60 carbon atoms in which aring-forming atom is a carbon atom only (e.g., the ring itself onlyincludes carbon atoms). The C₅-C₆₀ carbocyclic group may be an aromaticcarbocyclic group or a non-aromatic carbocyclic group. The C₅-C₆₀carbocyclic group may be a ring, such as benzene, a monovalent group,such as a phenyl group, or a divalent group, such as a phenylene group.In one or more embodiments, depending on the number of substituentsconnected to the C₅-C₆₀ carbocyclic group, the C₅-C₆₀ carbocyclic groupmay be a trivalent group or a quadrivalent group.

The term “C₁-C₆₀ heterocyclic group,” as used herein, refers to a grouphaving the same structure as the C₁-C₆₀ carbocyclic group, except thatas a ring-forming atom, at least one heteroatom selected from N, O, Si,P, and S is used in addition to carbon (the number of carbon atoms maybe in a range of 1 to 60).

At least one substituent of the substituted C₅-C₆₀ carbocyclic group,the substituted C₁-C₆₀ heterocyclic group, the substituted C₃-C₁₀cycloalkylene group, the substituted C₁-C₆₀ heterocycloalkylene group,the substituted C₃-C₁₀ cycloalkenylene group, the substituted C₁-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, thesubstituted C₁-C₆₀ heteroarylene group, the substituted divalentnon-aromatic condensed polycyclic group, the substituted divalentnon-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group may be selectedfrom:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C-Coo alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁)and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₆₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁),and —P(═O)(Q₃₁)(Q₃₂), and

Q₁₁ to Q₁₃, Q₂₁ to O₂₃, and Q₃₁ to Q₃₃ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

The term “Ph,” as used herein, refers to a phenyl group, the term “Me,”as used herein, refers to a methyl group, the term “Et,” as used herein,refers to an ethyl group, the term “ter-Bu” or “Bu^(t),” as used herein,refers to a tert-butyl group, and the term “OMe,” as used herein, refersto a methoxy group.

The term “biphenyl group,” as used herein, refers to “a phenyl groupsubstituted with a phenyl group.” In other words, the “biphenyl group”is a substituted phenyl group having a C₆-C₆₀ aryl group as asubstituent.

The term “terphenyl group,” as used herein, refers to “a phenyl groupsubstituted with a biphenyl group.” In other words, the “terphenylgroup” is a phenyl group having, as a substituent, a C₆-C₆₀ aryl groupsubstituted with a C₆-C₆₀ aryl group.

* and *′ used herein, unless defined otherwise, each refer to a bindingsite to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments and an organiclight-emitting device according to embodiments will be described in moredetail with reference to Synthesis Examples and Examples. The wording “Bwas used instead of A” used in describing Synthesis Examples refers tothat an identical (e.g., substantially identical) molar equivalent of Bwas used in place of A.

EXAMPLES Synthesis Example 1: Synthesis of Compound 2

Synthesis of Intermediate I-1

1.84 g (10 mmol) of cyanuric chloride was dissolved in 30 mL oftetrahydrofuran (THF), 26 mL of 4-fluorophenyl magnesium bromide (1.0 Min THF) was added thereto at a temperature of 0° C., and the reactionsolution was stirred at a temperature of 35° C. for 12 hours. Then, thereaction solution was cooled to room temperature, and an organic layerwas extracted therefrom three times by using 60 mL of water and 60 mL ofdiethylether. The extracted organic layer was dried by using magnesiumsulfate, and a solvent was evaporated therefrom. Then, the residueobtained therefrom was separated and purified by silica gel columnchromatography to obtain 1.36 g (yield: 45%) of Intermediate I-1. Theobtained compound was identified by LC-MS.

C₁₅H₈ClF₂N₃: M+1 303.4.

Synthesis of Intermediate I-2

3.34 g (11.0 mmol) of Intermediate I-1, 2.00 g (10.0 mmol) of4-bromophenyl boronic acid, 0.58 g (0.50 mmol) of Pd(PPh₃)₄, and 4.15 g(30.0 mmol) of K₂CO₃ were dissolved in 60 mL of a mixed solutionincluding THF and H₂O (2/1) and stirred at a temperature of 80° C. for16 hours. Then, the reaction solution was cooled to room temperature,and an organic layer was extracted therefrom three times by using 60 mLof water and 60 mL of diethylether. The extracted organic layer wasdried by using magnesium sulfate, and a solvent was evaporatedtherefrom. Then, the residue obtained therefrom was separated andpurified by silica gel column chromatography to obtain 2.12 g (yield:50%) of Intermediate I-2. The obtained compound was identified by LC-MS.

C₂₁H₁₂BrF₂N₃: M+1 423.0.

Synthesis of Compound 2

4.23 g (10 mmol) of Intermediate I-2, 1.98 g (10 mmol) of[1,1′-biphenyl]-4-ylboronic acid, 0.58 g (0.5 mmol) of Pd(PPh₃)₄, and4.14 g (30 mmol) of K₂CO₃ were dissolved in 60 mL of a mixed solutionincluding THF and H₂O (2/1) and stirred at a temperature of 80° C. for16 hours. Then, the reaction solution was cooled to room temperature,and an organic layer was extracted therefrom three times by using 40 mLof water and 50 mL of ethylether. The extracted organic layer was driedby using magnesium sulfate, and a solvent was evaporated therefrom.Then, the residue obtained therefrom was separated and purified bysilica gel column chromatography to obtain 4.08 g (yield: 82%) ofCompound 2. The obtained compound was identified by MS/FAB and ¹H NMR.

C₃₃H₂₁F₂N₃ cal. 497.17, found 497.16.

Synthesis Example 2: Synthesis of Compound 5

5.17 g (yield: 83%) of Compound 5 was synthesized in substantially thesame manner as in Synthesis of Compound 2, except that(4-(4-phenylnaphthalen-1-yl)phenyl)boronic acid was used instead of[1,1′-biphenyl]-4-ylboronic acid. The obtained compound was identifiedby MS/FAB and ¹H NMR.

C₄₃H₂₇F₂N₃ cal. 623.22, found 623.23.

Synthesis Example 3: Synthesis of Compound 9

4.73 g (yield: 76%) of Compound 9 was synthesized in substantially thesame manner as in Synthesis of Compound 2, except that(6-([1,1′-biphenyl]-4-yl)naphthalen-2-yl)boronic acid was used insteadof [1,1′-biphenyl]-4-ylboronic acid. The obtained compound wasidentified by MS/FAB and ¹H NMR.

C₄₃H₂₇F₂N₃ cal. 623.22, found 623.21.

Synthesis Example 4: Synthesis of Compound 25

4.42 g (yield: 72%) of Compound 25 was synthesized in substantially thesame manner as in Synthesis of Compound 2, except that(9,9-dimethyl-7-phenyl-9H-fluoren-2-yl)boronic acid was used instead of[1,1′-biphenyl]-4-ylboronic acid. The obtained compound was identifiedby MS/FAB and ¹H NMR.

C₄₂H₂₉F₂N₃ cal. 613.23, found 613.22.

Synthesis Example 5: Synthesis of Compound 31

3.03 g (10 mmol) of Intermediate I-1, 3.25 g (10 mmol) of(6-(3-(naphthalen-2-yl)phenyl)pyridin-2-yl)boronic acid, 0.58 g (0.5mmol) of Pd(PPh₃)₄, and 4.14 g (30 mmol) of K₂CO₃ were dissolved in 60mL of a mixed solution including THF and H₂O (2/1) and stirred at atemperature of 80° C. for 16 hours. Then, the reaction solution wascooled to room temperature, and an organic layer was extracted therefromthree times by using 40 mL of water and 50 mL of ethylether. Theextracted organic layer was dried by using magnesium sulfate, and asolvent was evaporated therefrom. Then, the residue obtained therefromwas separated and purified by silica gel column chromatography to obtain3.12 g (yield: 57%) of Compound 31. The obtained compound was identifiedby MS/FAB and ¹H NMR.

C₃₆H₂₂F₂N₄ cal. 548.18, found 548.19.

Synthesis Example 6: Synthesis of Compound 40

Synthesis of Intermediate I-3

2.25 g (10 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine was dissolvedin 30 mL of THF, 10 mL of 4-fluorophenyl magnesium bromide (1.0 M inTHF) was added thereto at a temperature of 0° C., and the reactionsolution was stirred at a temperature of 35° C. for 12 hours. Then, thereaction solution was cooled to room temperature, and an organic layerwas extracted therefrom three times by using 60 mL of water and 60 mL ofdiethylether. The extracted organic layer was dried by using magnesiumsulfate, and a solvent was evaporated therefrom. Then, the residueobtained therefrom was separated and purified by silica gel columnchromatography to obtain 1.31 g (yield: 46%) of Intermediate I-3. Theobtained compound was identified by LC-MS.

C₁₅H₉ClFN₃: M+1 285.1.

Synthesis of Intermediate I-4

2.03 g (yield: 50%) of Intermediate I-4 was synthesized in substantiallythe same manner as in Synthesis of Intermediate I-2, except thatintermediate I-3 was used instead of Intermediate I-1. The obtainedcompound was identified by LC-MS.

C₂₁H₁₃BrFN₃: M+1 405.0.

Synthesis of Compound 40

4.05 g (10 mmol) of Intermediate I-4, 2.48 g (10 mmol) of(4-(naphthalen-2-yl)phenyl)boronic acid, 0.58 g (0.5 mmol) of Pd(PPh₃)₄,and 4.14 g (30 mmol) of K₂CO₃ were dissolved in 60 mL of a mixedsolution including THF and H₂O (2/1) and stirred at a temperature of 80°C. for 16 hours. The reaction solution was cooled to room temperature,and an organic layer was extracted therefrom three times by using 40 mLof water and 50 mL of ethylether. The extracted organic layer was driedby using magnesium sulfate, and a solvent was evaporated therefrom.Then, the residue obtained therefrom was separated and purified bysilica gel column chromatography to obtain 4.07 g (yield: 77%) ofCompound 40. The obtained compound was identified by MS/FAB and ¹H NMR.

C₃₇H₂₄FN₃ cal. 529.20, found 529.21.

Synthesis Example 7: Synthesis of Compound 45

4.36 g (yield: 70%) of Compound 45 was synthesized in substantially thesame manner as in Synthesis of Compound 2, except that 3-fluorophenylmagnesium bromide was used instead of 4-fluorophenyl magnesium bromide,and (4′-(naphthalen-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid was usedinstead of [1,1′-biphenyl]-4-ylboronic acid. The obtained compound wasidentified by MS/FAB and ¹H NMR.

C₄₃H₂₇F₂N₃ cal. 623.22, found 623.22.

Synthesis Example 8: Synthesis of Compound 60

2.50 g (10 mmol) of 4-bromo-4′-fluoro-1,1′-biphenyl, 5.11 g (10 mmol) of2,4-diphenyl-6-(4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-4-yl)-1,3,5-triazine,0.58 g (0.5 mmol) of Pd(PPh₃)₄, and 4.14 g (30 mmol) of K₂CO₃ weredissolved in 60 mL of a mixed solution including THF and H₂O (2/1) andstirred at a temperature of 80° C. for 16 hours. Then, the reactionsolution was cooled to room temperature, and an organic layer wasextracted therefrom three times by using 40 mL of water and 50 mL ofethylether. The extracted organic layer was dried by using magnesiumsulfate, and a solvent was evaporated therefrom. Then, the residueobtained therefrom was separated and purified by silica gel columnchromatography to obtain 4.39 g (yield: 79%) of Compound 60. Theobtained compound was identified by MS/FAB and ¹H NMR.

C₃₉H₂₆FN₃ cal. 555.21, found 555.20.

Synthesis Example 9: Synthesis of Compound 74

2.98 g (10 mmol) of2-(4′-fluoro-[1,1′-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane,4.19 g (10 mmol) of2,4-di([1,1′-biphenyl]-4-yl)-6-chloro-1,3,5-triazine, 0.58 g (0.5 mmol)of Pd(PPh₃)₄, and 4.14 g (30 mmol) of K₂CO₃ were dissolved in 60 mL of amixed solution including THF and H₂O (2/1) and stirred at a temperatureof 80° C. for 16 hours. Then, the reaction solution was cooled to roomtemperature, and an organic layer was extracted therefrom three times byusing 40 mL of water and 50 mL of ethylether. The extracted organiclayer was dried by using magnesium sulfate, and a solvent was evaporatedtherefrom. Then, the residue obtained therefrom was separated andpurified by silica gel column chromatography to obtain 4.22 g (yield:76%) of Compound 74. The obtained compound was identified by MS/FAB and¹H NMR.

C₃₉H₂₆FN₃ cal. 555.21, found 555.20.

Synthesis Example 10: Synthesis of Compound 81

Synthesis of Intermediate I-5

4.35 g (10 mmol) of2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine,3.38 g (12 mmol) of 1-bromo-4-iodobenzene, 0.58 g (0.5 mmol) ofPd(PPh₃)₄, and 4.14 g (30 mmol) of K₂CO₃ were dissolved in 60 mL of amixed solution including THF and H₂O (2/1) and stirred at a temperatureof 80° C. for 16 hours. Then, the reaction solution was cooled to roomtemperature, and an organic layer was extracted therefrom three times byusing 40 mL of water and 50 mL of ethylether. Then extracted organiclayer was dried by using magnesium sulfate, and a solvent was evaporatedtherefrom. Then, the residue obtained therefrom was separated andpurified by silica gel column chromatography to obtain 3.38 g (yield:73%) of Intermediate I-5. The obtained compound was identified by LC-MS.

C₂₇H₁₈BrN₃: M+1 463.1.

Synthesis of Intermediate I-6

4.36 g (10 mmol) of Intermediate I-5, 2.54 g (10 mmol) ofbis(pinacolato)diboron, 0.35 g (0.5 mmol) of Pd(PPh₃)₂Cl₂, and 2.94 g(30 mmol) of KOAc were dissolved in 60 mL of toluene and stirred at atemperature of 100° C. for 16 hours. The reaction solution was cooled toroom temperature, and an organic layer was extracted therefrom threetimes by using 40 mL of water and 50 mL of ethylether. The extractedorganic layer was dried by using magnesium sulfate, and a solvent wasevaporated therefrom. Then, the residue obtained therefrom was separatedand purified by silica gel column chromatography to obtain 3.63 g(yield: 71%) of Intermediate I-6. The obtained compound was identifiedby LC-MS.

C₃₃H₃₀BN₃O₂: M+1 511.2.

Synthesis of Compound 81

3.03 g (10 mmol) of Intermediate I-1, 5.11 g (10 mmol) of IntermediateI-6, 0.58 g (0.5 mmol) of Pd(PPh₃)₄, and 4.14 g (30 mmol) of K₂CO₃ weredissolved in 60 mL of a mixed solution including THF and H₂O (2/1) andstirred at a temperature of 80° C. for 16 hours. Then, the reactionsolution was cooled to room temperature, and an organic layer wasextracted therefrom three times by using 40 mL of water and 50 mL ofethylether. The extracted organic layer was dried by using magnesiumsulfate, and a solvent was evaporated therefrom. Then, the residueobtained therefrom was separated and purified by silica gel columnchromatography to obtain 5.15 g (yield: 79%) of Compound 81. Theobtained compound was identified by MS/FAB and ¹H NMR.

C₄₂H₂₆F₂N₆ cal. 625.22, found 625.23.

Synthesis Example 11: Synthesis of Compound 90

Synthesis of Intermediate I-7

4.35 g (10 mmol) of2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine,3.38 g (12 mmol) of 1-bromo-4-iodobenzene, 0.58 g (0.5 mmol) ofPd(PPh₃)₄, and 4.14 g (30 mmol) of K₂CO₃ were dissolved in 60 mL of amixed solution including THF and H₂O (2/1) and stirred at a temperatureof 80° C. for 16 hours. Then, the reaction solution was cooled to roomtemperature, and an organic layer was extracted therefrom three times byusing 40 mL of water and 50 mL of ethylether. The extracted organiclayer was dried by using magnesium sulfate, and a solvent was evaporatedtherefrom. Then, the residue obtained therefrom was separated andpurified by silica gel column chromatography to obtain 3.38 g (yield:73%) of Intermediate I-5. The obtained compound was identified by LC-MS.

C₃₃H₃₀BN₃O₂: M+1 511.2.

Synthesis of Intermediate I-8

4.80 g (10 mmol) of Intermediate I-7, 2.54 g (10 mmol) ofbis(pinacolato)diboron, 0.35 g (0.5 mmol) of Pd(PPh₃)₂Cl₂, and 2.94 g(30 mmol) of KOAc were dissolved in 60 mL of toluene and stirred at atemperature of 100° C. for 16 hours. Then, the reaction solution wascooled to room temperature, and an organic layer was extracted therefromthree times by using 40 mL of water and 50 mL of ethylether. Theextracted organic layer was dried by using magnesium sulfate, and asolvent was evaporated therefrom. Then, the residue obtained therefromwas separated and purified by silica gel column chromatography to obtain3.70 g (yield: 70%) of Intermediate I-8. The obtained compound wasidentified by LC-MS.

C₃₆H₄₂B₂O₂: M+1 528.3.

Synthesis of Compound 90

5.28 g (10 mmol) of Intermediate I-8, 3.03 g (10 mmol) of2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine, 0.58 g (0.5 mmol) ofPd(PPh₃)₄, and 4.14 g (30 mmol) of K₂CO₃ were dissolved in 60 mL of amixed solution including THF and H₂O (2/1) and stirred at a temperatureof 80° C. for 16 hours. Then, the reaction solution was cooled to roomtemperature, and an organic layer was extracted therefrom three times byusing 40 mL of water and 50 mL of ethylether. The extracted organiclayer was dried by using magnesium sulfate, and a solvent was evaporatedtherefrom. Then, the residue obtained therefrom was separated andpurified by silica gel column chromatography to obtain 4.89 g (yield:73%) of Compound 90. The obtained compound was identified by MS/FAB and¹H NMR.

C₄₅H₃₈BF₂N₃ cal. 669.31, found 669.30.

¹H NMR and MS/FAB of the synthesized Compounds are shown in Table 1.Methods of synthesizing compounds other than Compounds shown in Table 1should be readily apparent to those of ordinary skill in the art byreferring to the synthesis mechanisms and source materials describedabove.

TABLE 1 Com- MS/FAB pound ¹H NMR (CDCl₃, 400 MHz) found calc. 2 δ =8.49-8.46 (m, 2H), 8.35-8.30 (m, 4H), 497.16 497.17 7.96-7.93 (M, 2H),7.72-7.65 (m, 4H), 7.61-7.58 (m, 2H), 7.53-7.49 (m, 2H), 7.42-7.39 (m,1H), 7.30-7.24 (m, 4H) 5 δ = 8.48-8.45 (m, 2H), 8.35-8.31 (m, 4H),623.23 623.22 8.05-8.01 (m, 2H), 7.96-7.93 (m, 2H), 7.52-7.78 (m, 2H),7.74-7.58 (m, 6H), 7.49-7.44 (m, 2H), 7.41-7.36 (m, 1H), 7.30-7.24 (m,4H), 7.01-6.96 (m, 2H) 9 δ = 8.53-8.50 (m, 2H), 8.35-8.31 (m, 4H),623.21 623.22 8.11 (dd, 2H), 7.97-7.91 (m, 4H), 7.72-7.66 (m, 6H),7.62-7.58 (m, 2H), 7.53-7.49 (m, 2H), 7.42-7.38 (m, 1H), 7.30-7.24 (m,4H) 25 δ = 8.52-8.48 (m, 2H), 8.35-8.30 (m, 4H), 613.22 613.23 7.91-7.87(m, 2H), 7.76-7.71 (m, 2H), 7.63-7.60 (m, 2H), 7.55-7.47 (m, 4H),7.42-7.38 (m, 1H), 7.31-7.24 (m, 6H), 1.56 (s, 6H) 31 δ = 8.56-8.52 (m,2H), 8.43-8.38 (m, 4H), 548.19 548.18 8.19-8.17 (m, 1H), 8.07-8.05 (m,1H), 8.00 (t, 1H), 7.93-7.91 (m, 1H), 7.89-7.77 (m, 4H), 7.72-7.69 (m,1H), 7.62-7.49 (m, 2H), 7.34-7.24 (m, 5H) 40 δ = 8.81-8.78 (m, 2H),8.49-8.46 (m, 2H), 529.21 529.20 8.35-8.30 (m, 2H), 8.09 (dd, 1H),7.96-7.85 (m, 5H), 7.77-7.49 (m, 9H), 7.42-7.39 (m, 1H), 7.30-7.25 (m,2H) 45 δ = 8.81-8.78 (m, 2H), 8.49-8.46 (m, 2H), 623.22 623.22 8.35-8.30(m, 2H), 8.10-8.08 (m, 1H), 7.96-7.85 (m, 5H), 7.77-7.49 (m, 9H),7.42-7.39 (m, 1H), 7.30-7.25 (m, 2H) 60 δ = 8.81-8.78 (m, 4H), 8.49-8.46(m, 2H), 555.20 555.21 7.96-7.93 (m, 2H), 7.76-7.59 (m, 12H), 7.42-7.38(m, 2H), 7.18-7.13 (m, 2H), 6.71-6.65 (m, 2H) 74 δ = 8.49-8.43 (m, 6H),8.00-7.92 (m, 6H), 555.20 555.21 7.60-7.58 (m, 4H), 7.52-7.49 (m, 4H),7.42-7.39 (m, 2H), 7.18-7.13 (m, 2H), 6.71-6.65 (m, 2H) 81 δ = 8.80-8.78(m, 4H), 8.65-8.64 (m, 2H), 625.23 625.22 8.59-8.56 (m, 2H), 8.35-8.30(m, 4H), 7.86-7.83 (m, 2H), 7.63-7.52 (m, 6H), 7.42-7.38 (m, 2H),7.30-7.24 (m, 4H) 90 δ = 8.49-8.46 (m, 2H), 8.35-8.30 (m, 4H), 669.30669.31 7.97-7.93 (m, 2H), 7.67-7.64 (m, 2H), 7.56-7.53 (m, 2H),7.30-7.24 (m, 4H), 6.80-6.77 (m, 4H), 2.19 (s, 18H)

Methods of synthesizing compounds other than the Compounds synthesizedaccording to Synthesis Examples 1 to 11 may also be readily apparent tothose of ordinary skill in the art by referring to the synthesismechanisms and source materials described above.

Example 1

As an anode, a Corning 15 Ω/cm² (1,200 Å) ITO glass substrate was cut toa size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol and purewater each for 5 minutes, and then cleaned by exposure to ultravioletrays and ozone for 30 minutes. Then, the resultant ITO glass substratewas provided to a vacuum deposition apparatus.

2-TNATA, which is a generally available material, was vacuum-depositedon the anode to form a hole injection layer having a thickness of 600 Å,and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), which is agenerally available material, was vacuum-deposited as a hole transportcompound on the hole injection layer to form a hole transport layerhaving a thickness of 300 Å.

9,10-di-naphthalene-2-yl-anthracene (ADN) and4,4′-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), whichare generally available compounds, were respectively co-deposited as ablue fluorescent host and a blue fluorescent dopant on the holetransport layer at a weight ratio of 98:2 to form an emission layerhaving a thickness of 300 Å.

Then, Compound 2 was deposited on the emission layer to form an electrontransport layer having a thickness of 300 Å, LiF, which is an alkalimetal halide, was deposited on the electron transport layer to form anelectron injection layer having a thickness of 10 Å, and Al wasvacuum-deposited on the electron injection layer to form a cathodeelectrode having a thickness of 3,000 Å, thereby forming a LiF/Alelectrode. In this manner, an organic light-emitting device wasmanufactured.

Example 2

An organic light-emitting device was manufactured in substantially thesame manner as in Example 1, except that Compound 5 was used instead ofCompound 2 in forming an electron transport layer.

Example 3

An organic light-emitting device was manufactured in substantially thesame manner as in Example 1, except that Compound 9 was used instead ofCompound 2 in forming an electron transport layer.

Example 4

An organic light-emitting device was manufactured in substantially thesame manner as in Example 1, except that Compound 25 was used instead ofCompound 2 in forming an electron transport layer.

Example 5

An organic light-emitting device was manufactured in substantially thesame manner as in Example 1, except that Compound 31 was used instead ofCompound 2 in forming an electron transport layer.

Example 6

An organic light-emitting device was manufactured in substantially thesame manner as in Example 1, except that Compound 40 was used instead ofCompound 2 in forming an electron transport layer.

Example 7

An organic light-emitting device was manufactured in substantially thesame manner as in Example 1, except that Compound 45 was used instead ofCompound 2 in forming an electron transport layer.

Example 8

An organic light-emitting device was manufactured in substantially thesame manner as in Example 1, except that Compound 60 was used instead ofCompound 2 in forming an electron transport layer.

Example 9

An organic light-emitting device was manufactured in substantially thesame manner as in Example 1, except that Compound 74 was used instead ofCompound 2 in forming an electron transport layer.

Example 10

An organic light-emitting device was manufactured in substantially thesame manner as in Example 1, except that Compound 81 was used instead ofCompound 2 in forming an electron transport layer.

Example 11

An organic light-emitting device was manufactured in substantially thesame manner as in Example 1, except that Compound 90 was used instead ofCompound 2 in forming an electron transport layer.

Comparative Example 1

An organic light-emitting device was manufactured in substantially thesame manner as in Example 1, except that Compound 200 was used insteadof Compound 2 in forming an electron transport layer.

Comparative Example 2

An organic light-emitting device was manufactured in substantially thesame manner as in Example 1, except that Compound 201 was used insteadof Compound 2 in forming an electron transport layer.

Comparative Example 3

An organic light-emitting device was manufactured in substantially thesame manner as in Example 1, except that Compound 202 was used insteadof Compound 2 in forming an electron transport layer.

The driving voltage, luminance, efficiency (cd/A), and half lifespan ofthe organic light-emitting devices manufactured according to Examples 1to 11 and Comparative Examples 1 to 3 were measured at a current densityof 50 mA/cm², and results thereof are shown in Table 2 below.

TABLE 2 Driving Current Half voltage density Luminance EfficiencyEmission lifespan Material (V) (mA/cm²) (cd/m²) (cd/A) color (hr @ 100mA/cm²) Example 1 Compound 2 3.65 50 3,705 7.41 Blue 710 hr Example 2Compound 5 3.63 50 3,890 7.78 Blue 706 hr Example 3 Compound 9 3.60 503,775 7.55 Blue 721 hr Example 4 Compound 25 3.69 50 3,750 7.50 Blue 759hr Example 5 Compound 31 3.62 50 3,790 7.58 Blue 732 hr Example 6Compound 40 3.64 50 3,820 7.64 Blue 745 hr Example 7 Compound 45 3.60 503,815 7.63 Blue 720 hr Example 8 Compound 60 3.55 50 3,785 7.57 Blue 726hr Example 9 Compound 74 3.58 50 3,795 7.59 Blue 733 hr Example 10Compound 81 3.61 50 3,800 7.60 Blue 750 hr Example 11 Compound 90 3.5950 3,810 7.62 Blue 738 hr Comparative Compound 200 3.85 50 3,555 7.11Blue 633 hr Example 1 Comparative Compound 201 3.90 50 3,570 7.14 Blue656 hr Example 2 Comparative Compound 202 4.32 50 3,500 7.00 Blue 602 hrExample 3

From Table 2, when the compound according to one or more embodiments wasused as an electron transport material, excellent I-V-L characteristicsincluding a low driving voltage and remarkably improved efficiency andluminance were exhibited, as compared with Compounds 201 to 202 as wellas Compound 200, which are generally available materials. For example,an excellent lifespan improvement effect was exhibited.

For example, when the compound according to one or more embodiments isused as an electron transport material of a device, excellent effectsmay be exhibited in terms of driving voltage, luminance, efficiency, andlifespan. Compounds 2, 5, 9, 25, 31, 40, 45, 60, 74, 81, and 90 areshown below.

An organic light-emitting device according to an embodiment may have alow driving voltage, high efficiency, and a long lifespan.

It will be understood that, although the terms “first,” “second,”“third,” etc., may be used herein to describe various elements,components, regions, layers and/or sections, these elements, components,regions, layers and/or sections should not be limited by these terms.These terms are used to distinguish one element, component, region,layer or section from another element, component, region, layer orsection. Thus, a first element, component, region, layer or sectiondescribed below could be termed a second element, component, region,layer or section, without departing from the spirit and scope of thepresent disclosure.

Spatially relative terms, such as “beneath,” “below,” “lower,” “under,”“above;” “upper,” and the like, may be used herein for ease ofexplanation to describe one element or feature's relationship to anotherelement(s) or feature(s) as illustrated in the figures. It will beunderstood that the spatially relative terms are intended to encompassdifferent orientations of the device in use or in operation, in additionto the orientation depicted in the figures. For example, if the devicein the figures is turned over, elements described as “below” or“beneath” or “under” other elements or features would then be oriented“above” the other elements or features. Thus, the example terms “below”and “under” can encompass both an orientation of above and below.

The device may be otherwise oriented (e.g., rotated 90 degrees or atother orientations) and the spatially relative descriptors used hereinshould be interpreted accordingly.

It will be understood that when an element or layer is referred to asbeing “on,” “connected to,” or “coupled to” another element or layer, itcan be directly on, connected to, or coupled to the other element orlayer, or one or more intervening elements or layers may be present. Inaddition, it will also be understood that when an element or layer isreferred to as being “between” two elements or layers, it can be theonly element or layer between the two elements or layers, or one or moreintervening elements or layers may also be present.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting of the presentdisclosure. As used herein, the singular forms “a” and “an” are intendedto include the plural forms as well, unless the context clearlyindicates otherwise. It will be further understood that the terms“comprises,” “comprising,” “includes,” and “Including,” when used inthis specification, specify the presence of the stated features,integers, acts, operations, elements, and/or components, but do notpreclude the presence or addition of one or more other features,integers, acts, operations, elements, components, and/or groups thereof.

As used herein, the terms “substantially,” “about,” and similar termsare used as terms of approximation and not as terms of degree, and areintended to account for the inherent deviations in measured orcalculated values that would be recognized by those of ordinary skill inthe art. Further, the use of “may” when describing embodiments of thepresent disclosure refers to “one or more embodiments of the presentdisclosure.” As used herein, the terms “use,” “using,” and “used” may beconsidered synonymous with the terms “utilize,” “utilizing,” and“utilized,” respectively.

Also, any numerical range recited herein is intended to include allsub-ranges of the same numerical precision subsumed within the recitedrange. For example, a range of “1.0 to 10.0” is intended to include allsubranges between (and including) the recited minimum value of 1.0 andthe recited maximum value of 10.0, that is, having a minimum value equalto or greater than 1.0 and a maximum value equal to or less than 10.0,such as, for example, 2.4 to 7.6. Any maximum numerical limitationrecited herein is intended to include all lower numerical limitationssubsumed therein, and any minimum numerical limitation recited in thisspecification is intended to include all higher numerical limitationssubsumed therein. Accordingly, Applicant reserves the right to amendthis specification, including the claims, to expressly recite anysub-range subsumed within the ranges expressly recited herein.

It should be understood that embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments.

While one or more embodiments have been described with reference to thefigures, it will be understood by those of ordinary skill in the artthat various changes in form and details may be made therein withoutdeparting from the spirit and scope as defined by the following claims.

What is claimed is:
 1. A heterocyclic compound represented by Formula 1:

wherein, in Formula 1, L₁ to L₃ are each independently selected from asingle bond and groups represented by Formulae 3-1 and 3-4 to 3-29:

wherein, in Formulae 3-1 and 3-4 to 3-29, Y₁ may be C(Z₃)(Z₄) orSi(Z₆)(Z₇), Z₁ to Z₇ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, a silolyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, adibenzosilolyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), a1 to a3 are eachindependently an integer from 1 to 5, R₁ to R₃ may each independently beselected from: a phenyl group, a biphenyl group, a terphenyl group, apentalenyl group, an indenyl group, a naphthyl group, an azulenyl group,a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a pyrenyl group, a chrysenylgroup, a naphthacenyl group, a picenyl group, a perylenyl group, apentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenylgroup, a coronenyl group, an ovalenyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a thiophenyl group, a furanyl group, a quinolinyl group, anisoquinolinyl group, a benzofuranyl group, a benzothiophenyl group, adibenzosilolyl group, a benzonaphthosilolyl group, a dinaphthosilolylgroup, a benzimidazolyl group, a phenanthrolinyl group, and animidazopyridinyl group; a phenyl group, a biphenyl group, a terphenylgroup, a pentalenyl group, an indenyl group, a naphthyl group, anazulenyl group, a heptalenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, atriazinyl group, a thiophenyl group, a furanyl group, a quinolinylgroup, an isoquinolinyl group, a benzofuranyl group, a benzothiophenylgroup, a dibenzosilolyl group, a benzonaphthosilolyl group, adinaphthosilolyl group, a benzimidazolyl group, a phenanthrolinyl group,and an imidazopyridinyl group, each substituted with at least oneselected from deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group,a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a pyrenyl group, a chrysenylgroup, a naphthacenyl group, a picenyl group, a perylenyl group, apentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenylgroup, a coronenyl group, an ovalenyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a thiophenyl group, a furanyl group, a quinolinyl group, anisoquinolinyt group, a benzofuranyl group, a benzothiophenyl group, adibenzosilolyl group, —N(Q₃₁)(Q₃₂), and —Si(Q₃₁)(Q₃₂)(Q₃₃); and 13N(Q₁)(Q₂) and —B(Q₁)(Q₂), and Q₁, Q₂, and Q₃₁ to Q₃₃ are eachindependently selected from: a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a biphenyl group, a terphenyl group, a naphthylgroup, and a pyridinyl group; and a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, and a pyridinyl group, eachsubstituted with a C₁-C₂₀ alkyl group or a C₁-C₂₀ alkoxy group b1 to b3are each independently an integer from 1 to 20, at least one selectedfrom R₁ to R₃ is a fluoro-containing cyclic group and at least oneselected from R₁ to R₃ does not include a fluoro-containing cyclicgroup, each fluoro-containing cyclic group contains one to four fluorineatoms, when at least one of R₁(s) in the number of b1 is thefluoro-containing cyclic group, L₁ is not a substituted or unsubstitutedtriazine group, when at least one of R₂(s) in the number of b2 is thefluoro-containing cyclic group, L₂ is not a substituted or unsubstitutedtriazine group, and when at least one of R₃(s) in the number of b3 isthe fluoro-containing cyclic group, L₃ is not a substituted orunsubstituted triazine group, the heterocyclic compound does not includea carbazole group, a benzocarbazole group, a dibenzofuran group, adibenzothiophene group, and a triphenylene group, and * indicates abinding site to a neighboring atom.
 2. The heterocyclic compound ofclaim 1, wherein: L₁ to L₃ are each independently selected from: asingle bond, a pentalene group, an indene group, a naphthalene group, anazulene group, a heptalene group, an indacene group, an acenaphthalenegroup, a fluorene group, a spiro-bifluorene group, aspiro-benzofluorene-fluorene group, a benzofluorene group, adibenzofluorene group, a phenalene group, a phenanthrene group, ananthracene group, a fluoranthene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, a pyrrolegroup, a thiophene group, a furan group, a silole group, an imidazolegroup, a pyrazole group, a thiazole group, an isothiazole group, anoxazole group, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, a triazine group, a benzofurangroup, a benzothiophene group, a benzosilole group, a dibenzosilolegroup, a quinoline group, an isoquinoline group, a benzimidazole group,an imidazopyridine group, and an imidazopyrimidine group; and a benzenegroup, a pentalene group, an indene group, a naphthalene group, anazulene group, a heptalene group, an indacene group, an acenaphthalenegroup, a fluorene group, a spiro-bifluorene group, aspiro-benzofluorene-fluorene group, a benzofluorene group, adibenzofluorene group, a phenalene group, a phenanthrene group, ananthracene group, a fluoranthene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, a pyrrolegroup, a thiophene group, a furan group, a silole group, an imidazolegroup, a pyrazole group, a thiazole group, an isothiazole group, anoxazole group, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, a triazine group, a benzofurangroup, a benzothiophene group, a benzosilole group, a dibenzosilolegroup, a quinoline group, an isoquinoline group, a benzimidazole group,an imidazopyridine group, and an imidazopyrimidine group, eachsubstituted with at least one selected from deuterium, —Cl, —Br, —I, ahydroxyl group, a cyano group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, a heptalenyl group, an indacenylgroup, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coronenyl group, anovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzofuranyl group,a benzothiophenyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and—B(Q₃₁)(Q₃₂), and Q₁ and Q₃₁ to Q₃₃ are each independently selected froma C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, and a pyridinyl group. 3.The heterocyclic compound of claim 1, wherein: a1 to a3 are eachindependently an integer from 1 to
 3. 4. The heterocyclic compound ofclaim 1, wherein: R₁ to R₃ are each independently selected from: aphenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a pyrenyl group, a chrysenyl group, anaphthacenyl group, a picenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a rubicenyl group, acoronenyl group, an ovalenyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, athiophenyl group, a furanyl group, a quinolinyl group, an isoquinolinylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzosilolylgroup, a benzonaphthosilolyl group, a dinaphthosilolyl group, abenzimidazolyl group, a phenanthrolinyl group, and an imidazopyridinylgroup; a phenyl group, a biphenyl group, a terphenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a pyrenyl group, a chrysenylgroup, a naphthacenyl group, a picenyl group, a perylenyl group, apentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenylgroup, a coronenyl group, an ovalenyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a thiophenyl group, a furanyl group, a quinolinyl group, anisoquinolinyl group, a benzofuranyl group, a benzothiophenyl group, adibenzosilolyl group, a benzonaphthosilolyl group, a dinaphthosilolylgroup, a benzimidazolyl group, a phenanthrolinyl group, and animidazopyridinyl group, each substituted with at least one selected fromdeuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group,an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a biphenyl group, a terphenyl group, a pentalenyl group, anindenyl group, a naphthyl group, an azulenyl group, a heptalenyl group,an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a pyrenyl group, a chrysenyl group, anaphthacenyl group, a picenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a rubicenyl group, acoronenyl group, an ovalenyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, athiophenyl group, a furanyl group, a quinolinyl group, an isoquinolinylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzosilolylgroup, —N(Q₃₁)(Q₃₂), and —Si(Q₃₁)(Q₃₂)(Q₃₃); and —N(Q₁)(Q₂) and—B(Q₁)(Q₂), and Q₁, Q₂, and Q₃₁ to Q₃₃ are each independently selectedfrom: a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, abiphenyl group, a terphenyl group, a naphthyl group, and a pyridinylgroup; and a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, and a pyridinyl group, each substituted with a C₁-C₂₀alkyl group or a C₁-C₂₀ alkoxy group.
 5. The heterocyclic compound ofclaim 1, wherein: the fluoro-containing cyclic group comprises one ortwo fluoro groups.
 6. The heterocyclic compound of claim 1, wherein: thefluoro-containing cyclic group is a C₃-C₆₀ carbocyclic group substitutedwith at least one —F.
 7. The heterocyclic compound of claim 1, wherein:the fluoro-containing cyclic group is a C₆-C₆₀ aryl group or amonovalent non-aromatic condensed polycyclic group, each substitutedwith at least one —F.
 8. A heterocyclic compound represented by Formula1: Formula 1

wherein, in Formula 1, L₁ to L₃ are each independently selected from asingle bond and groups represented by Formulae 3-1 and 3-4 to 3-29:

wherein, in Formulae 3-1 and 3-4 to 3-29, Y₁ may be C(Z₃)(Z₄) orSi(Z₆)(Z₇), Z₁ to Z₇ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, a silolyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, adibenzosilolyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), a1 to a3 are eachindependently an integer from 1 to 5, R₁ to R₃ are each independentlyselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₂-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₂-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₂-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), and—B(Q₁)(Q₂), b1 to b3 are each independently an integer from 1 to 20, atleast one selected from R₁ to R₃ is a fluoro-containing cyclic group andat least one selected from R₁ to R₃ does not include a fluoro-containingcyclic group, each fluoro-containing cyclic group contains one to fourfluorine atoms, when at least one of R₁(s) in the number of b1 is thefluoro-containing cyclic group, L₁ is not a substituted or unsubstitutedtriazine group, when at least one of R₂(s) in the number of b2 is thefluoro-containing cyclic group, L₂ is not a substituted or unsubstitutedtriazine group, and when at least one of R₃(s) in the number of b3 isthe fluoro-containing cyclic group, L₃ is not a substituted orunsubstituted triazine group, the heterocyclic compound does not includea carbazole group, a benzocarbazole group, a dibenzofuran group, adibenzothiophene group, and a triphenylene group, at least onesubstituent of the substituted C₃-C₆₀ carbocyclic group, the substitutedC₁-C₆₀ heterocyclic group, the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₂-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₂-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₂-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group is selected from: deuterium, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group; aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group, each substituted with at least one selected fromdeuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group,an amidino group, a hydrazino group, a hydrazono group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃),—N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), and —C(═O)(Q₁₁); a C₃-C₁₀ cycloalkyl group,a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, a biphenyl group, and a terphenylgroup; a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, each substituted with at least oneselected from deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, a biphenyl group, a terphenyl group,—Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), and —C(═O)(Q₂₁); and—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), and —C(═O)(Q₃₁), Q₁ toQ₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ are each independentlyselected from hydrogen, deuterium, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryl groupsubstituted with a C₁-C₆₀ alkyl group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, a biphenyl group, and aterphenyl group, * indicates a binding site to a neighboring atom, andwherein: the fluoro-containing cyclic group is selected from groupsrepresented by Formulae 4-1 to 4-19:

wherein, in Formulae 4-1 to 4-19, Y₃₁ is O, S, C(Z₃₃)(Z₃₄), N(Z₃₃), orSi(Z₃₃)(Z₃₄), Z₃₁ and Z₃₂ are each independently selected from hydrogen,deuterium, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group,an amino group, an amidino group, a hydrazine group, a hydrazone group,a carboxylic acid group or a salt thereof, a sulfonic acid group or asalt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, atriazinyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₂₀ alkyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), Q₃₁ toQ₃₃ are each independently selected from a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, apyrimidinyl group, a triazinyl group, a biphenyl group, a terphenylgroup, and a phenyl group substituted with a C₁-C₂₀ alkyl group, e2 isan integer from 0 to 2, e3 is an integer from 0 to 3, e4 is an integerfrom 0 to 4, e6 is an integer from 0 to 6, and * indicates a bindingsite to a neighboring atom.
 9. The heterocyclic compound of claim 1,wherein: i) when at least one of R₁(s) in the number of b1 is thefluoro-containing cyclic group, at least one of L₁(s) in the number ofa1 is a single bond or a substituted or unsubstituted C₃-C₆₀ carbocyclicgroup, ii) at least one of R₂(s) in the number of b2 is thefluoro-containing cyclic group, at least one of L₂(s) in the number ofa2 is a single bond or a substituted or unsubstituted C₃-C₆₀ carbocyclicgroup, or iii) at least one of R₃(s) in the number of b3 is thefluoro-containing cyclic group, at least one of L₃(s) in the number ofa3 is a single bond or a substituted or unsubstituted C₃-C₆₀ carbocyclicgroup, and the substituent of the substituted C₃-C₆₀ carbocyclic groupis selected from a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀ alkoxy group.
 10. The heterocyclic compoundof claim 9, wherein: the substituted or unsubstituted C₃-C₆₀ carbocyclicgroup is selected from: a benzene group, a naphthalene group, and afluorene group; and a benzene group and a fluorene group, eachsubstituted with a C₁-C₂₀ alkyl group.
 11. The heterocyclic compound ofclaim 1, wherein: i) at least one of R₁(s) in the number of b1 is afluoro-containing cyclic group, and R₂(s) in the number of b2 and R₃(s)in the number of b3 are each independently selected from: a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, and apyridinyl group; and a triazinyl group substituted with one or morephenyl groups; or ii) at least one of R₁(s) in the number of b1 and atleast one of R₂(s) in the number of b2 are each a fluoro-containingcyclic group, and R₃(s) in the number of b3 are each independentlyselected from: a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a pyridinyl group, a fluorenyl group, an anthracenylgroup, a phenanthrenyl group, a quinolinyl group, a phenanthrolinylgroup, a triazinyl group, and a pyrimidinyl group; a phenyl group, abiphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group,a fluorenyl group, an anthracenyl group, a phenanthrenyl group, aquinolinyl group, a phenanthrolinyl group, a triazinyl group, and apyrimidinyl group, each substituted with at least one selected from acyano group, a C₁-C₂₀ alkyl group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group,an anthracenyl group, a phenanthrenyl group, a triazinyl group, and apyrimidinyl group; and —B(Q₁)(Q₂); and Q₁ and Q₂ are each a substitutedphenyl group substituted with one or more C₁-C₂₀ alkyl groups.
 12. Aheterocyclic compound, wherein: the heterocyclic compound is selectedfrom Compounds 1 to 90:


13. An organic light-emitting device comprising: a first electrode; asecond electrode facing the first electrode; and an organic layerbetween the first electrode and the second electrode, wherein theorganic layer comprises an emission layer and at least one of theheterocyclic compound of claim
 1. 14. The organic light-emitting deviceof claim 13, wherein: the first electrode is an anode, the secondelectrode is a cathode, the organic layer further comprises a holetransport region between the first electrode and the emission layer andan electron transport region between the emission layer and the secondelectrode, the hole transport region comprises a hole injection layer, ahole transport layer, an emission auxiliary layer, an electron blockinglayer, or any combination thereof, and the electron transport regioncomprises a buffer layer, a hole blocking layer, an electron controllayer, an electron transport layer, an electron injection layer, or anycombination thereof.
 15. The organic light-emitting device of claim 14,wherein: the electron transport region comprises the heterocycliccompound.
 16. The organic light-emitting device of claim 14, wherein:the electron transport region comprises an electron transport layerwhich includes the heterocyclic compound.
 17. The organic light-emittingdevice of claim 16, wherein: the electron transport region comprises anemission auxiliary layer, and the emission auxiliary layer comprises theheterocyclic compound.
 18. The organic light-emitting device of claim14, wherein: the hole transport region comprises a p-dopant, and thep-dopant has a lowest unoccupied molecular orbital (LUMO) energy levelof −3.5 eV or less.
 19. The organic light-emitting device of claim 18,wherein: the p-dopant comprises a cyano group-containing compound. 20.The organic light-emitting device of claim 13, wherein: the emissionlayer is a first emission layer for emitting first color light, theorganic light-emitting device further comprises, between the firstelectrode and the second electrode, i) at least one second emissionlayer for emitting second color light or ii) at least one secondemission layer for emitting second color light and at least one thirdemission layer for emitting third color light, a maximum emissionwavelength of the first color light, a maximum emission wavelength ofthe second color light, and a maximum emission wavelength of the thirdcolor light are identical to or different from one another, and thefirst color light and the second color light are emitted in the form ofmixed light, or the first color light, the second color light, and thethird color light are emitted in the form of mixed light.